SODIUM PERBORATE

1

Sodium Perborate

NaBO

3

⋅4H

2

O

[10486-00-7]

BH

8

NaO

7

(MW 153.88)

InChI = 1/B2H4O8.2Na.2H2O/c3-1(4)7-9-2(5,6)10-8-1;;;;/

h3-6H;;;2*1H2/q-2;2*+1;;

InChIKey = SJZZCOLEHYXGTA-UHFFFAOYAU

(oxidizing agent for a variety of functional groups)

Physical Data:

mp 60

◦

C (dec.); bulk density 0.74–0.82 g cm

−3

.

Solubility:

sol water (∼23 g L

−1

at 20

◦

C, ∼37 g L

−1

at 30

◦

C;

pH of 1% solution ∼10.4); sol acetic acid, lower alcohols.

Form Supplied in:

colorless, crystalline, odorless, free-flowing

powder; widely available; 96% minimum sodium perborate
tetrahydrate; 10% minimum available oxygen.

Handling, Storage, and Precautions:

safe when handled cor-

rectly. It should be stored in a cool, dry place (below 40

◦

C)

protected from direct heat and humidity.

Original Commentary

Alexander McKillop
University of East Anglia, Norwich, UK

‘Sodium perborate tetrahydrate’, NaBO

3

·4H

2

O, has the

1,4-diboratetraoxane structure (1). This structure is disrupted in
polar protic solvents such as water, alcohols, and carboxylic acids,
and various types of oxidizing species can be generated, from the
perhydroxyl anion to protonated perboric acid, depending on
the pH. The reagent is most commonly used in acetic acid at tem-
peratures between ambient and 60

◦

C; peracetic acid is produced

at appreciable rates at higher temperatures. Detailed mechanisms
for the various perborate oxidations have yet to be established.
In most of its applications, sodium perborate is recommended
as a cheap, safe, and convenient alternative to oxidants such as
Hydrogen Peroxide, Peracetic Acid and m-Chloroperbenzoic
Acid, especially for large scale operations.

O

O

O

O

OH

B

B

OH

–

HO

OH

(1)

–

2Na

+

•6H

2

O

Functional Group Oxidations.

Sulfur and Selenium. Thiols (RSH) and selenols (RSeH) are

smoothly oxidized in high yield to disulfides (RSSR) and di-
selenides (RSeSeR).

1

Many sulfides, including a range of hetero-

cyclic sulfur compounds, have been oxidized cleanly to sulfones
with excess reagent (eq 1).

2

–

5

Conversion of sulfides into sul-

foxides also proceeds in high yield when 1 equiv of oxidant is
used, although in most cases small amounts of sulfones are also
formed.

2,6

Chiral sulfoxides are obtained from appropriate pre-

cursors (eq 2).

7

Oxidation at sulfur and selenium is faster than at

most other functional groups and hence it is not usually necessary
to protect amino, hydroxyl, or alkenic centers. In the presence of
Acetic Anhydride, sodium perborate is an effective reagent for the
preparation of α,β-unsaturated carbonyl compounds by oxidative
deselenylation of α-phenylselenocarbonyl derivatives (eq 3).

8

S

H
N

S
O

2

H
N

(1)

NaBO

3

•4H

2

O

AcOH

45–50

°C

75%

S

NMe

2

Me

S

NMe

2

Me

O

–

S

NMe

2

Me

O

–

(2)

+

+

+

10%

72%

78% de

rt

NaBO

3

•4H

2

O

AcOH

O

C

5

H

11

O

PhSe

O

C

5

H

11

O

NaBO

3

•4H

2

O

Ac

2

O, THF

rt

(3)

90%

Nitrogen.

Oxidation of π-deficient azines (substituted

pyridines, pyrazines, and quinolines; isoquinoline) with sodium
perborate in acetic acid gives good yields of the corresponding
N

-oxides.

5,9

The reactions of anilines are particularly interest-

ing. Depending on the reaction conditions, they can be converted
into the corresponding azo,

10

–

12

azoxy,

13

or nitro

2,14

compounds

(eq 4). The latter transformation is particularly useful for anilines
which contain powerful electron-withdrawing groups in the ortho
or para positions (eq 5).

2

Excellent yields are obtained of products

which are very difficult, or impossible, to prepare by standard
aromatic substitution reactions. Primary aliphatic amines are
oxidised to C-nitroso compounds

15

(isolated in good yield as the

dimers), while oximes give moderate yields of the corresponding
nitro compounds.

16

N,N

-Dialkylhydrazones are cleaved to the

ketones in good to excellent yield.

2,17

N NAr

ArN NAr

Ar

–

O

(4)

ArNH

2

+ NaBO

3

•4H

2

O

+

ArNO

2

Avoid Skin Contact with All Reagents

2

SODIUM PERBORATE

(5)

X = 4-CF

3

, 86%; 2-O

2

N, 76%; 4-NC, 91%

XC

6

H

4

NO

2

XC

6

H

4

NH

2

Alkenes and Alkynes. Most types of alkenes react rather slug-

gishly with sodium perborate in acetic acid and this process is of
little use for epoxidation. A mixture of the perborate with acetic
anhydride, however, apparently generates peroxybis(diacetoxy-
borane), (AcO)

2

B–O–O–B(OAc)

2

, which does epoxidize alkenes

in good yield (eq 6).

18

Use of the same reagent system with Sulfu-

ric Acid catalysis gives 1,2-diol monoacetates (eq 7). Similar types
of products are obtained from a series of α-substituted styrenes
with perborate in acetic acid (eq 8),

19

while terminal alkynes

give 1-acetoxyalkan-2-ones with added Mercury(II) Acetate as
catalyst.

20

Epoxidation of α,β-unsaturated ketones can be effected

in excellent yield either under phase-transfer conditions

21

or sim-

ply by using sodium perborate in a two phase water–THF system
(eq 9).

22

Epoxidation of quinones has been described,

23

but in

most cases yields are low.

O

(6)

NaBO

3

•4H

2

O

Ac

2

O, CH

2

Cl

2

70%

rt

OAc

OH

(7)

NaBO

3

•4H

2

O

Ac

2

O, H

2

SO

4

reflux

59%

(8)

NaBO

3

•4H

2

O

AcOH

55

°C

4-BrC

6

H

4

SPh

4-BrC

6

H

4

SO

2

Ph

AcO

OH

78%

(9)

O

O

O

NaBO

3

•4H

2

O

THF–H

2

O

reflux

92%

Alcohols, Aldehydes, Ketones, Phenols, and Nitriles. Simple

alcohols react only very slowly with sodium perborate and, as in-
dicated below, aqueous alcohol serves as a very suitable solvent
for the hydration of nitriles. Benzylic alcohols are oxidized to
aldehydes, ketones, and/or carboxylic acids only at temperatures
higher than 60

◦

C.

24

α

-Hydroxy acids are oxidized to ketones

or carboxylic acids, 1,2-diols are cleaved to acids and ketones,
and α-diketones also give carboxylic acids.

25

Room temperature

Baeyer–Villiger oxidation of ketones proceeds smoothly (eq 10),

2

while perborate/acetic acid at 45–50

◦

C is an excellent reagent

for the high yield oxidation of a wide range of aromatic aldehy-
des to the corresponding carboxylic acids.

5,26

Hydroquinones and

certain highly substituted phenols are oxidized in good yield to
quinones.

2

The phenol oxidations may involve initial electrophilic

hydroxylation of the electron-rich rings.

11,27

Although not for-

mally an oxidation, the hydration of nitriles by perborate is a clean

and high yielding reaction.

5,28,29

Interestingly, there is no reac-

tion when acetic acid is used as solvent, but use of water, aqueous
methanol, or a water–dioxane system gives excellent results.

MeO

COMe

MeO

OCOMe

(10)

rt

NaBO

3

•4H

2

O

AcOH

81%

Boron, Iodine, Phosphorus. Trialkyl- and triarylboranes are

efficiently converted into alcohols and phenols on treatment
at room temperature with sodium perborate in a water–THF
system.

30,31

Oxidation at boron is even faster than oxidation at

sulfur (eq 11), and the perborate oxidation is as good as, or bet-
ter than, the conventional peroxide/base procedure. It is particu-
larly useful for the clean, high yield conversion of alkenylboranes
into aldehydes and ketones.

32

Iodoarenes are readily oxidised by

sodium perborate. Use of acetic acid as solvent gives good yields
of (diacetoxyiodo)arenes (eq 12),

5

while (dichloroiodo)arenes,

ArICl

2

, are obtained in 60–98% yield when hydrochloric acid

is used.

33

Sodium perborate has been recommended as a viable

alternative to hydrogen peroxide for the large scale oxidative
decomposition of toxic organophosphorus ester wastes.

34

–

36

S

S

(11)

OH

2. NaBO

3

•4H

2

O

H

2

O, 25 °C

92%

1. BH

3

•THF, 0

°C

ArI

ArI(OCOMe)

2

(12)

NaBO

3

•4H

2

O

AcOH

40–50

°C

66–80%

First Update

George W. Kabalka & Marepally Srinivasa Reddy
University of Tennessee, Knoxville, TN, USA

Molybdenum(VI) effectively catalyzes sodium perborate (SPB)

oxidation of dimethyl and dibenzyl sulfoxides to sulfones in
glacial acetic acid (yields in the 80% range) (eq 13).

37

The oxida-

tions are zero-order with respect to the oxidant and first-order with
respect to Mo(VI) and the sulfoxides. The addition of trichloro-
acetic acid enhances the oxidations while methanol, ethylene
glycol, and water suppress the reactions. The kinetic results
revealed dioxoperoxomolybdenum(VI) is the reactive oxidant.

R

S

O

R

R

S

O

O

R

Na

2

MoO

4

, AcOH

50-60

°C

(13)

NaBO

3

⋅4H

2

O, DMSO

Nitrogen.

Microwave irradiation of several aromatic and

aliphatic nitriles, including an α,β-bistrimethysilylnitrile, with
sodium perborate tetrahydrate in a mixture of water/ethanol (2:1)
produced the corresponding amide (eq 14)

38

rapidly and in high

A list of General Abbreviations appears on the front Endpapers

SODIUM PERBORATE

3

yields. Other functional groups, such as the aldehyde and tri-
methylsilyl groups, are unaffected under these conditions. Treat-
ment of C,N-diarylaldimines with sodium perborate tetrahy-
drate in trifluoroacetic acid at 70 – 80

◦

C results in an oxidative

rearrangement to N,N-diarylformamides (eq 15).

39,40

15

N-

Labelled trimethylpyrazine can be oxidized to a mixture of
1-, 4-, and di-N-oxides by SPB in acetic acid.

41

In a study involv-

ing the N-hydroxylation of azoles using MCPBA, H

2

O

2

–formic

acid, or SPB in pivalic acid, the latter was found to be superior to
MCPBA for the preparation of N-hydroxytetrazoles (eq 16).

42

CN

OHC

OHC

O

NH

2

H

2

O, ethanol, MW

97%

(14)

NaBO

3

⋅4H

2

O

NaBO

3

⋅4H

2

O

Ar

1

H

NAr

2

N

O

H

Ar

1

Ar

2

(15)

CF

3

CO

2

H, 70–80

°C

N

N

N

N H

N

N

N

N OH

N

N

N

N

OH

SPB/t-BuCO

2

H

100

°C 3 h

+

33%

17%

(16)

Halogenation of Aromatic Compounds.

Halogenation of

aromatic compounds is readily achieved using aqueous haloacids
(HCl and HBr) with SPB as the oxidizing agent in the pres-
ence of tetrabutylammonium bromide (TBAB) as a phase-transfer
catalyst (eq 17).

43

Activated benzene rings undergo halogenation

smoothly to yield a mixture of both ortho and para substituted
products, whereas deactivated rings do not halogenate even after
prolonged reaction times.

R

X

NaBO

3

⋅4H

2

O, HX

R

(17)

1,2-dichloroethane

TBAB, 65

°C

O

B O O

B

O

OH

OH

OH

HO

HX

H

+

HOX

HO

B

O

O

H

OH

X

2

R

TBAB

2NaCl

X

R

2

+

H

3

BO

3

+H

2

O

2

Sodium perborate and potassium bromide

44

(or potassium

iodide

45

) in glacial acetic acid—acetic anhydride, with sodium

tungstate as a catalyst, provides a novel system for the bromina-
tion (or iodination) of aromatic amides (eq 18). Sodium perborate
can also be used for selective monobromination of various deac-
tivated anilines using potassium bromide and ammonium molyb-
date (eq 19)

46

as catalyst. The catalyst accelerates the rate of

reaction but is not essential for obtaining good yields and high
selectivities.

NaBO

3

⋅4H

2

O

HN

O

CH

3

HN

O

CH

3

X

(18)

X = Br or I

X = Br or I

AcOH-Ac

2

O, Na

2

WO

4

KX

R

R

Br

NH

2

NaBO

3

⋅4H

2

O, KBr

AcOH, (NH

4

)

6

Mo

7

O

24

⋅4H

2

O

NH

2

(19)

Thiocyanation of arenes using SPB with ammonium thiocyanate

in glacial acetic acid at room temperature gives the corresponding
thiocyanato compounds (eq 20).

47

The reaction produces good to

excellent yields of the desired product. It has been observed that
only activated and heteroaromatic rings undergo thiocyanation
smoothly. It is interesting to note that aniline undergoes thiocya-
nation without affecting the amino group, possibly because thio-
cyanogen (SCN)

2

is instantly formed in situ Therefore, aniline

undergoes thiocyanation without oxidation under the conditions
used.

NH

2

NH

4

SCN

NaBO

3

⋅H

2

O

CH

3

COOH

NH

2

SCN

(20)

+

Alcohols and Phenols. Sodium perborate has been used for

the selective oxidation of secondary alcohols in the presence of
primary alcoholic and other functional groups using a catalytic
amount of aqueous HBr in AcOH at 50

◦

C to give the correspond-

ing ketones (eq 21)

48

in excellent yields.

R

1

R

2

H

OH

SPB, aq HBr (20 mol %)

R

1

R

2

O

AcOH, 50

°C

(21)

Sodium perborate in boron trifluoride etherate (1:5 mol ratio)

has been found to be an effective reagent for the hydroperoxide
rearrangement of electron rich and highly substituted benzylic
tertiary alcohols to phenols (eq 22).

49

The reaction is incomplete

when the ratio of SPB to boron trifluoride etherate was 1:4 or 1:3,
even after 24 h.

NaBO

3

⋅4H

2

O

OH

R

O OH

R

OH

R

BF

3

Et

2

O, THF

(22)

A variety of aryl acetates are selectively cleaved to the corre-

sponding phenols (eq 23)

50

using SPB in methanol under mild

conditions (25

◦

C). The effectiveness of this protocol is manifested

Avoid Skin Contact with All Reagents

4

SODIUM PERBORATE

in its tolerance of functional groups. Deprotection of aryl acetates
occurs readily whereas alkyl acetates are found to be unreactive
under the reaction conditions.

ArO

O

CH

3

Ar–OH

MeO

O

CH

3

+

NaBO

3

/MeOH

25

°C

(23)

Calix[4] crown-4-ether can be conveniently oxidized by sodium

perborate tetrahydrate in trifluoroacetic acid to afford the mono-
quinone (eq 24). Diamide calix[4] and diester calix[4] crown-
4-ethers are also oxidized using sodium perborate tetrahydrate
in trifluoroacetic acid to give the corresponding diquinones.

51

O

OH OH

O

O

O

NaBO

3

⋅

4H

2

O

CF

3

COOH

O

OH O

O

O

O

O

(24)

Aldehydes and Ketones. Sodium perborate has been used

to oxidize aldehydes to esters

52

in the presence of a mineral acid

(such as 70% HClO

4

) using vanadium pentaoxide (V

2

O

5

) as cata-

lyst in an alcoholic medium. The oxidation is carried out by adding
70% HClO

4

over a period of time to a mixture containing alde-

hyde, catalyst (V

2

O

5

), SPB, and alcohol. Sodium perborate/acetic

anhydride is very effective and highly selective for the oxidative
cleavage of acetals to their respective esters (eq 25).

53

NaBO

3

⋅4H

2

O/Ac

2

O

R

O

O

R

O

O

Na

2

CO

3

, C

6

H

6

, 55

°C

OR´

(25)

An efficient and convenient method has been developed for the

conversion of 2-hydroxy phenyl ketoxime to 1,2-benzisoxazole-
2-oxide with SPB in glacial acetic acid under mild reaction con-
ditions (eq 26).

54

Interestingly, when the reaction is carried out

under reflux, deoximation is observed.

R

5

OH

N OH

R

1

R

2

R

4

R

AcOH, Reflux

NaBO

3

⋅4H

2

O

AcOH, 45–55

°C

OH

R

1

R

4

R

5

O

R

2

R

O

R

N

O

R

5

R

1

R

2

R

4

(26)

NaBO

3

⋅4H

2

O

Decarbonylation of imidazo-2-yl and pyrid-2-ylpyruvic acids

to give the corresponding acetic acids has been achieved using
aqueous SPB at room temperature. It is proposed that intramolec-
ular hydrogen bonding, which inhibits conventional decarbonyl-
ation, facilitates epoxidation and subsequent decarboxylation of
the enol tautomers (eq 27).

55

N

N

O

CO

2

H

Me

O

2

N

SPB

N

N

Me

O

2

N

O

H

O

O

O

CO

2

N

N

O

Me

O

2

N

O

H

H

+

N

N

CO

2

H

Me

O

2

N

Me

O

2

N

O

H

N

N

CO

2

H

(27)

Baeyer–Villiger Oxidation.

Sodium perborate/formic acid

mixtures have found wide application in the formation of sim-
ple monocyclic lactones.

56

Chloroketo acid A (eq 28) is smoothly

converted by sodium perborate tetrahydrate in formic acid to the
chloroketolactone B in 66% isolated yield. The reaction is com-
pletely regioselective in favor of the bridgehead-migrated isomer
B. Transesterification of β-keto esters with various alcohols
has been carried out using SPB as a catalyst under neutral condi-
tions (eq 29).

57

The effectiveness of the protocol is manifested in

its selectivity toward β-keto esters, whereas other esters are found
to be unreactive under these reaction conditions.

HOOC

Cl

O

HOOC

Cl

O

A

NaBO

3

⋅4H

2

O

B

HCOOH, 66%

(28)

O

O

OR

1

R

2

OH

O

O

R

1

OH

NaBO

3

+

Toluene/

OR

2

+

(29)

Alkenes, Iodoarenes, and Boranes. A series of α,β-unsatu-

rated ketones has been treated with SPB in water and 1,4-dioxane
under microwave irradiation to produce α,β-epoxy ketones in
good yields (eq 30).

58

Sodium perborate, with potassium per-

manganate as a catalyst, has been shown to be a novel reagent
for the epoxidation of steroidal 5-enes with attack occurring pre-
dominantly on the β-face.

59

Sodium perborate is also used for the

Julia asymmetric epoxidation of enones

60

other than chalcones in

the presence of polyleucine as catalyst. Yields are excellent and
good enantiomeric excess (ee) values are observed. Bromination
of alkenes with sodium bromide in the presence of SPB in acetic
acid provided high yields of dibromoalkanes (eq 31).

61

The re-

action of the iodoarenes with SPB in acetic acid in the presence
of trifluoromethanesulfonic acid (triflic acid) at 40–45

◦

C rapidly

A list of General Abbreviations appears on the front Endpapers

SODIUM PERBORATE

5

generates the corresponding (diacetoxyiodo)arenes (eq 32)

62

in

high yields (86–99%). Addition of triflic acid as a promoter causes
a dramatic increase in the yield of (diacetoxyiodo)arenes in
reactions of iodoarenes with SPB. The presence of CF

3

SO

3

H

(in stoichiometric quantities) in the reaction mixture consider-
ably enhances the oxidizing activity. When CF

3

SO

3

H is replaced

by concentrated H

2

SO

4

, the final yields of ArI(OAc)

2

are not

improved. The SPB–HOAc system has also been used in the
preparation of various chiral hypervalent iodine compounds
(eq 33).

63

R

4

R

3

O

R

1

R

2

H

2

O, 1,4-dioxane

O

R

4

R

1

R

2

R

3

O

MW 2–3 min, NaBO

3

⋅4H

2

O

(30)

NaBO

3

⋅4H

2

O

COOH

COOH

Br

Br

NaBr, AcOH

(31)

R

AcOH

I(OAc)

2

R

NaBO

3

⋅4H

2

O, CF

3

COOH

I

+

3–8 h, 40–45

°C, 86–99%

(32)

I

Et

OMe

Et

OMe

OH

OTos

Et

OMe

Et

OMe

I

1. NaBO

3

⋅4H

2

O, AcOH

2. p-TosOH, CH

3

CN

55%

(33)

.

A convenient approach has been developed for iodolactoni-

sation using iodobenzene as catalyst. The active reagent was gene-
rated in situ with tetra-n-butylammonium iodide (TBAI) and a
hypervalent iodine reagent, diacetoxyiodobenzene (PIDA). PIDA,
in turn, was generated in situ using a catalytic amount of iodoben-
zene with sodium perborate monohydrate as the stoichiomet-
ric oxidant. A variety of olefinic acids, including δ-pentenoic
acids, δ-pentynoic acids, and δ-hexynoic acid, gave high yields of
lactones. (eq 34).

64

R

1

R

2

CO

2

H

R

3

I

O

O

R

1

R

2

I

R

3

5 mol %

(34)

n

-Bu

4

NI 1.1 equiv

NaBO

3

⋅H

2

O 2 equiv

AcOH 5 equiv

CH

2

Cl

2

, 40

°C

Sodium perborate has been shown to be especially useful for

oxidizing organoborane intermediates. Primary alcohols can be
prepared selectively from terminal alkenes in the presence of
ketone and aldehyde groups by hydroboration followed by SPB
oxidation.

65

For example, 5-methylhex-5-en-2-one is converted

into 6-hydroxy-5-methylhexan-2-one (eq 35) using SPB follow-
ing hydroboration with dicyclohexylborane formed in situ from
BH

3

–THF and cyclohexene. Terminal alkynes are similarly trans-

formed into aldehydes.

66

The same general approach has been

used to prepare (+)-isopinocampheol stereospecifically from (+)-
α

-pinene in 92% overall yield.

67

A route to alkyl aryl carbinols

from α,α-dichlorotoluenes and trialkylboranes also utilized SPB
in the workup for oxidative cleavage of the organoborane.

68,69,70

The same overall transformation can be affected using the corre-
sponding benzaldehyde trisyl-

71

or tosylhydrazone

72

as the source

of the aryl moiety, with yields generally being superior in the trisyl
series (eq 36).

O

O

HO

(35)

BH

3

-THF, Cyclohexene

THF, 0

°C, 1 h

NaBO

3

⋅4H

2

O, H

2

O

THF, rt, 2 h

80%

N

NHTris

BR

2

R

NaBO

3

⋅4H

2

O

H

2

O

X

X

R

3

B

X

OH

R

Base

(36)

Related Reagents. Hydrogen Peroxide; Sodium Percarbonate

(SPC); meta-Chloroperbenzoic Acid (MCPBA).

1.

McKillop, A.; Koyuncu, D.; Krief, A.; Dumont, W.; Renier, P.; Trabelsi,
M., Tetrahedron Lett. 1990, 31, 5007.

2.

McKillop, A.; Tarbin, J. A., Tetrahedron 1987, 43, 1753.

3.

Ding, X.; Ge, Y.; Teng, Z.; Fan, J., Yiyao Gongye 1987, 18, 193.

4.

Page, G. O., Synth. Commun. 1993, 23, 765.

5.

McKillop, A.; Kemp, D., Tetrahedron 1989, 45, 3299.

6.

Karunakaran, C.; Manimekalai, P., Tetrahedron 1991, 47, 8733.

7.

Shimazaki, M.; Takahashi, M.; Komatsu, H.; Ohta, A.; Kajii, K.;
Komada, Y., Synthesis 1992, 555.

8.

Kabalka, G. W.; Reddy, N. K.; Narayana, C., Synth. Commun. 1993, 23,
543.

9.

Ohta, A.; Ohta, M., Synthesis 1985, 216.

10.

Mehta, S. M.; Vakilwala, M. V., J. Am. Chem. Soc. 1952, 74, 563.

11.

Santurri, P.; Robbins, F.; Stubbings, R., Org. Synth., Coll. Vol. 1973, 5,
341.

12.

Ogata, Y.; Shimizu, H., Bull. Chem. Soc. Jpn. 1979, 52, 635.

13.

Ding, X.; Teng, Z.; Ge, Y., Youji Huaxue 1989, 9, 257 (Chem. Abstr.
1990, 112, 35 351y).

14.

Holt, D. A.; Levy, M. A.; Yen, H.-K.; Oh, H.-J.; Metcalf, B. W.; Wier,
P. J., Bioorg. Med. Chem. Lett. 1991, 1, 27.

15.

Zajac, W. W., Jr.; Darcy, M. G.; Subong, A. P.; Buzby, J. H., Tetrahedron
Lett. 1989

, 30, 6495.

16.

Olah, G. A.; Ramaiah, P.; Lee, C.-S.; Prakash, G. K. S., Synlett 1992,
337.

17.

Enders, D.; Bhushan, V., Z. Naturforsch., Tell B 1987, 42, 1595.

18.

Xie, G.; Xu, L.; Hu, J.; Ma, S.; Hou, W.; Tao, F., Tetrahedron Lett. 1988,
29

, 2967.

19.

Gupton, J. T.; Duranceau, S. J.; Miller, J. F.; Kosiba, M. L., Synth.
Commun. 1988

, 18, 937.

20.

Reed, K. L.; Gupton, J. T.; McFarlane, K. L., Synth. Commun. 1989, 19,
2595.

21.

Dehmlow, E. V.; Vehre, B., Nouv. J. Chim. 1989, 13, 117.

22.

Reed, K. L.; Gupton, J. T.; Solarz, T. L., Synth. Commun. 1989, 19, 3579.

23.

Rashid, A.; Read, G., J. Chem. Soc. (C) 1967, 1323.

24.

Muzart, J.; N’Ait Ajjou, A., Synth. Commun. 1991, 21, 575.

25.

Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.;
Sengupta, S., Synthesis 1989, 765.

Avoid Skin Contact with All Reagents

6

SODIUM PERBORATE

26.

Xu, F.; Wang, J., Shanghai Keji Daxue Xuebao 1988, 11, 118 (Chem.
Abstr. 1990

, 112, 76 519c).

27.

Prakash, G. K. S.; Krass, N.; Wang, Q.; Olah, G. A., Synlett 1991, 39.

28.

Jammot, J.; Pascal, R.; Commeyras, A., Tetrahedron Lett. 1989, 30,
563.

29.

Reed, K. L.; Gupton, J. T.; Solarz, T. L., Synth. Commun. 1990, 20,
563.

30.

Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M., Tetrahedron Lett. 1989,
30

, 1483.

31.

Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M., J. Org. Chem. 1989,
54

, 5930.

32.

Matteson, D. S.; Moody, R. J., J. Org. Chem. 1980, 45, 1091.

33.

Koyuncu, D.; McKillop, A.; McLaren, L., J. Chem. Res. (S) 1990,
21.

34.

Kenley, R. A.; Lee, G. C.; Winterle, J. S., J. Org. Chem. 1985, 50,
40.

35.

Cristau, H.-J.; Torreilles, E.; Ginieys, J.-F., Heteroatom Chem. 1990, 1,
277.

36.

Cristau, H.-J.; Torreilles, E.; Ginieys, J.-F., J. Chem. Soc., Perkin Trans.
2 1991

, 13.

37.

Karunakaran, C.; Venkataramanan, R., Catal. Commun. 2006, 7,
236.

38.

Sharifi, A.; Mohsenzadeh, F.; Mojtahedi, M. M.; Saidi, M. R.; Balalaie,
B., Synth. Commun. 2001, 31, 431.

39.

Nongkunsarn, P.; Ramsden, C. A., Tetrahedron Lett. 1993, 34, 6773.

40.

Nongkunsarn, P.; Ramsden, C. A., Tetrahedron 1997, 53, 3805.

41.

Maeda, M.; Sakuma, C.; Kawachi, S.; Tabei, K.; Kerim, A.; Kurihara,
T.; Akihiro Ohta, A., J. Labelled Compd. Radiopharm. 1995, 36, 85.

42.

Begtrup, M.; Vedsø, P., J. Chem. Soc., Perkin Trans. 1 1995, 243.

43.

Deshmukh, A. P.; Padiya, K. J.; Jadhav, V. K.; Manikrao M.; Salunkhe,
M. M., J. Chem. Res. (S) 1998, 828.

44.

Hanson, J. R.; Harpel, S.; Rodriguez Medina, I. C.; Rose, D., J. Chem.
Res. (S) 1997

, 432.

45.

Beinker, P.; Hanson, J. R.; Meindl, N.; Rodriguez Medina, I. C., J.
Chem. Res. (S) 1998

, 204.

46.

Roche, D.; Prasad, K.; Repic, O.; Blacklock, T. J., Tetrahedron Lett.
2000, 41, 2083.

47.

Jadhav, V. K.; Pal, R. R.; Wadgaonkar, P. P.; Salunkhe, M. M., Synth.
Commun. 2001

, 31, 3041.

48.

Jain, S. L.; Sharma, V. B.; Sain, B., Tetrahedron 2006, 62,
6841.

49.

Kabalka, G. W.; Reddy, N. K.; Narayana, C., Tetrahedron Lett. 1993, 34,
7667.

50.

Bandgar, B. P.; Uppalla, L. S.; Sadavarte, V. S.; V. Patil, S. V., New J.
Chem. 2002

, 26, 1273.

51.

Chen, C.-F.; Zheng, Q.-Y.; Huang, Z.-T., Synthesis 1999, 69

52.

Gopinath, R.; Barkakaty, B.; Talukdar, B.; Patel, B. K., J. Org. Chem.
2003, 68, 2944.

53.

Bhat, S.; Ramesha, A. R.; Chandrasekharan, S., Synlett 1995, 16, 329.

54.

Jadhav, V. K.; Deshmukh, A. P.; Wadagaonkar, P. P.; Salunkhe, M. M.,
Synth. Commun. 2000

, 30, 1521.

55.

Ramsden, C. A.; Sargent, B. J.; Wallett, C. D., Tetrahedron Lett. 1996,
37

, 1901.

56.

Okabayashi, N.; Mitamura, S. (Shinnittetsu Kagaku), Jpn. Kokai Tokkyo
Koho, JP 08127578; Chem. Abstr. 1996

, 125, 142586.

57.

Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S., Chem. Lett. 2001, 894.

58.

Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F., J. Chem. Res. (S) 1998,
668.

59.

Hanson, J. R.; Terry, N.; Uyanik, C., J. Chem. Res. (S) 1998, 50.

60.

Lasterra-Sgnchez, M. E.; Felfer, U.; Mayon, P.; Roberts, S. M.; Thornton,
S. R.; Todd, C. J., J. Chem. Soc., Perkin Trans. 1 1996, 343.

61.

Kabalka, G. W.; Yang, K.; Reddy, N. K.; Narayana, C., Synth. Commun.
1998, 28, 925.

62.

Hossain, Md. D.; Kitamura, T., J. Org. Chem. 2005, 70, 6984.

63.

Wirth, T.; Hirt, U. H., Tetrahedron: Asymmetry 1997, 8, 23.

64.

Liu, H.; Tan, C.-H., Tetrahedron Lett. 2007, 48, 8220.

65.

Kabalka, G. W.; Yu, S.; Li, N.-S., Tetrahedron Lett. 1997, 38, 5455.

66.

Kabalka, G. W.; Yu, S.; Li, N.-S., Tetrahedron Lett. 1997, 38, 7681.

67.

Kabalka, G. W.; Maddox, J. T.; Shoup, T.; Bowers, K. R., Org. Synth.
1996, 73, 116.

68.

Kabalka, G. W.; Li, N.-S.; Yu, S., Tetrahedron Lett. 1995, 36, 8545.

69.

Li, N.-S.; Su, Y.; Kabalka, G. W., J. Organomet. Chem. 1997, 531, 101.

70.

Li, N.-S.; Su, Y.; Kabalka, G. W., Organometallics 1997, 16, 709.

71.

Kabalka, G. W.; Maddox, J. T.; Bogas, E.; Tejedor, D.; Ross, E. J., Synth.
Commun. 1996

, 26, 999.

72.

Kabalka, G. W.; Maddox, J. T.; Bogas, E.; Kelley, S. W., J. Org. Chem.
1997, 62, 3688.

A list of General Abbreviations appears on the front Endpapers