SODIUM PERBORATE 1
Sodium Perborate 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-
NaBO3Å"4H2O
cursors (eq 2).7 Oxidation at sulfur and selenium is faster than at
most other functional groups and hence it is not usually necessary
[10486-00-7] BH8NaO7 (MW 153.88)
to protect amino, hydroxyl, or alkenic centers. In the presence of
InChI = 1/B2H4O8.2Na.2H2O/c3-1(4)7-9-2(5,6)10-8-1;;;;/
Acetic Anhydride, sodium perborate is an effective reagent for the
h3-6H;;;2*1H2/q-2;2*+1;;
preparation of Ä…,²-unsaturated carbonyl compounds by oxidative
InChIKey = SJZZCOLEHYXGTA-UHFFFAOYAU
deselenylation of Ä…-phenylselenocarbonyl derivatives (eq 3).8
(oxidizing agent for a variety of functional groups)
NaBO3" 4H2O
H H
ć% AcOH
N N
Physical Data: mp 60 C (dec.); bulk density 0.74 0.82 g cm-3.
45 50 °C
ć% ć%
(1)
Solubility: sol water (<"23 g L-1 at 20 C, <"37 g L-1 at 30 C;
75%
pH of 1% solution <"10.4); sol acetic acid, lower alcohols. S S
O2
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-
ć% NaBO3" 4H2O
rectly. It should be stored in a cool, dry place (below 40 C)
NMe2 AcOH
protected from direct heat and humidity.
rt
Me
S
Original Commentary NMe2 NMe2
+ (2)
+ +
Me Me
S S
Alexander McKillop
University of East Anglia, Norwich, UK O O
10% 72%
 Sodium perborate tetrahydrate , NaBO3·4H2O, has the 78% de
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 C5H11 NaBO3" 4H2O
C5H11
perhydroxyl anion to protonated perboric acid, depending on Ac2O, THF
rt
O
the pH. The reagent is most commonly used in acetic acid at tem- O
(3)
ć%
peratures between ambient and 60 C; peracetic acid is produced
PhSe 90%
O
O
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
Nitrogen. Oxidation of Ä„-deficient azines (substituted
Hydrogen Peroxide, Peracetic Acid and m-Chloroperbenzoic
pyridines, pyrazines, and quinolines; isoquinoline) with sodium
Acid, especially for large scale operations.
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
OH
into the corresponding azo,10 12 azoxy,13 or nitro2,14 compounds

B
OH
(eq 4). The latter transformation is particularly useful for anilines
O
O 2Na+" 6H2O
which contain powerful electron-withdrawing groups in the ortho
O
 O
HO
or para positions (eq 5).2 Excellent yields are obtained of products
B
which are very difficult, or impossible, to prepare by standard
OH
aromatic substitution reactions. Primary aliphatic amines are
(1)
oxidised to C-nitroso compounds15 (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
Functional Group Oxidations.
Sulfur and Selenium. Thiols (RSH) and selenols (RSeH) are ArN NAr
smoothly oxidized in high yield to disulfides (RSSR) and di-

O
+
selenides (RSeSeR).1 Many sulfides, including a range of hetero-
ArNH2 + NaBO3" 4H2O N NAr (4)
cyclic sulfur compounds, have been oxidized cleanly to sulfones
Ar
with excess reagent (eq 1).2 5 Conversion of sulfides into sul-
ArNO2
Avoid Skin Contact with All Reagents
2 SODIUM PERBORATE
XC6H4NH2 XC6H4NO2 (5)
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
X = 4-CF3, 86%; 2-O2N, 76%; 4-NC, 91%
methanol, or a water dioxane system gives excellent results.
NaBO3" 4H2O
COMe OCOMe
Alkenes and Alkynes. Most types of alkenes react rather slug-
AcOH
(10)
gishly with sodium perborate in acetic acid and this process is of rt
MeO MeO
81%
little use for epoxidation. A mixture of the perborate with acetic
anhydride, however, apparently generates peroxybis(diacetoxy-
borane), (AcO)2B O O B(OAc)2, which does epoxidize alkenes
in good yield (eq 6).18 Use of the same reagent system with Sulfu- Boron, Iodine, Phosphorus. Trialkyl- and triarylboranes are
ric Acid catalysis gives 1,2-diol monoacetates (eq 7). Similar types efficiently converted into alcohols and phenols on treatment
of products are obtained from a series of Ä…-substituted styrenes at room temperature with sodium perborate in a water THF
with perborate in acetic acid (eq 8),19 while terminal alkynes system.30,31 Oxidation at boron is even faster than oxidation at
give 1-acetoxyalkan-2-ones with added Mercury(II) Acetate as sulfur (eq 11), and the perborate oxidation is as good as, or bet-
catalyst.20 Epoxidation of Ä…,²-unsaturated ketones can be effected ter than, the conventional peroxide/base procedure. It is particu-
in excellent yield either under phase-transfer conditions21 or sim- larly useful for the clean, high yield conversion of alkenylboranes
ply by using sodium perborate in a two phase water THF system into aldehydes and ketones.32 Iodoarenes are readily oxidised by
(eq 9).22 Epoxidation of quinones has been described,23 but in sodium perborate. Use of acetic acid as solvent gives good yields
most cases yields are low. of (diacetoxyiodo)arenes (eq 12),5 while (dichloroiodo)arenes,
ArICl2, are obtained in 60 98% yield when hydrochloric acid
is used.33 Sodium perborate has been recommended as a viable
NaBO3" 4H2O
O
Ac2O, CH2Cl2 alternative to hydrogen peroxide for the large scale oxidative
rt
decomposition of toxic organophosphorus ester wastes.34 36
(6)
70%
S S OH
1. BH3" THF, 0 °C
NaBO3" 4H2O (11)
2. NaBO3" 4H2O
Ac2O, H2SO4
OAc
H2O, 25 °C
reflux
(7) 92%
59%
OH
NaBO3" 4H2O
AcOH
(12)
40 50 °C
ArI ArI(OCOMe)2
NaBO3" 4H2O
66 80%
AcOH
4-BrC6H4
4-BrC6H4
55 °C
AcO SO2Ph
(8)
SPh
78%
OH
First Update
NaBO3" 4H2O
OO
THF H2O
George W. Kabalka & Marepally Srinivasa Reddy
reflux
(9) University of Tennessee, Knoxville, TN, USA
O
92%
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-
Alcohols, Aldehydes, Ketones, Phenols, and Nitriles. Simple
tions are zero-order with respect to the oxidant and first-order with
alcohols react only very slowly with sodium perborate and, as in-
respect to Mo(VI) and the sulfoxides. The addition of trichloro-
dicated below, aqueous alcohol serves as a very suitable solvent
acetic acid enhances the oxidations while methanol, ethylene
for the hydration of nitriles. Benzylic alcohols are oxidized to
glycol, and water suppress the reactions. The kinetic results
aldehydes, ketones, and/or carboxylic acids only at temperatures
revealed dioxoperoxomolybdenum(VI) is the reactive oxidant.
ć%
higher than 60 C.24 Ä…-Hydroxy acids are oxidized to ketones
or carboxylic acids, 1,2-diols are cleaved to acids and ketones,
O
O O
and Ä…-diketones also give carboxylic acids.25 Room temperature NaBO3Å"4H2O, DMSO
S
S
(13)
Baeyer Villiger oxidation of ketones proceeds smoothly (eq 10),2
Na2MoO4, AcOH
R R
R R
ć%
while perborate/acetic acid at 45 50 C is an excellent reagent 50-60 °C
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 Nitrogen. Microwave irradiation of several aromatic and
quinones.2 The phenol oxidations may involve initial electrophilic aliphatic nitriles, including an Ä…,²-bistrimethysilylnitrile, with
hydroxylation of the electron-rich rings.11,27 Although not for- sodium perborate tetrahydrate in a mixture of water/ethanol (2:1)
mally an oxidation, the hydration of nitriles by perborate is a clean produced the corresponding amide (eq 14)38 rapidly and in high
A list of General Abbreviations appears on the front Endpapers
SODIUM PERBORATE 3
O
yields. Other functional groups, such as the aldehyde and tri-
O
methylsilyl groups, are unaffected under these conditions. Treat-
HN CH3
HN CH3
ment of C,N-diarylaldimines with sodium perborate tetrahy-
NaBO3Å"4H2O
ć%
(18)
drate in trifluoroacetic acid at 70  80 C results in an oxidative
AcOH-Ac2O, Na2WO4
rearrangement to N,N-diarylformamides (eq 15).39,40 15N-
KX
Labelled trimethylpyrazine can be oxidized to a mixture of
X X = Br or I
1-, 4-, and di-N-oxides by SPB in acetic acid.41 In a study involv-
X = Br or I
ing the N-hydroxylation of azoles using MCPBA, H2O2 formic
NH2
NH2
acid, or SPB in pivalic acid, the latter was found to be superior to
MCPBA for the preparation of N-hydroxytetrazoles (eq 16).42
NaBO3Å"4H2O, KBr
R (19)
R
AcOH, (NH4)6Mo7O24Å"4H2O
O
Br
CN
NaBO3Å"4H2O NH2
Thiocyanation of arenes using SPB with ammonium thiocyanate
H2O, ethanol, MW
(14)
OHC
OHC
in glacial acetic acid at room temperature gives the corresponding
97%
thiocyanato compounds (eq 20).47 The reaction produces good to
excellent yields of the desired product. It has been observed that
Ar1
O
NaBO3Å"4H2O Ar1
only activated and heteroaromatic rings undergo thiocyanation
NAr2 (15)
N
CF3CO2H, 70 80 °C
H Ar2
H smoothly. It is interesting to note that aniline undergoes thiocya-
nation without affecting the amino group, possibly because thio-
N
N cyanogen (SCN)2 is instantly formed in situ Therefore, aniline
SPB/t-BuCO2H N
N H + (16)
N OH
N N
undergoes thiocyanation without oxidation under the conditions
N
N
100 °C 3 h
N N
N
used.
OH 17%
33%
NH2
NH2
NaBO3Å"H2O
NH4SCN
+
(20)
Halogenation of Aromatic Compounds. Halogenation of
CH3COOH
aromatic compounds is readily achieved using aqueous haloacids
(HCl and HBr) with SPB as the oxidizing agent in the pres-
SCN
ence of tetrabutylammonium bromide (TBAB) as a phase-transfer
catalyst (eq 17).43 Activated benzene rings undergo halogenation
Alcohols and Phenols. Sodium perborate has been used for
smoothly to yield a mixture of both ortho and para substituted
the selective oxidation of secondary alcohols in the presence of
products, whereas deactivated rings do not halogenate even after
primary alcoholic and other functional groups using a catalytic
prolonged reaction times.
ć%
amount of aqueous HBr in AcOH at 50 C to give the correspond-
R
R
ing ketones (eq 21)48 in excellent yields.
NaBO3Å"4H2O, HX
R1 H SPB, aq HBr (20 mol %) R1
(17)
O (21)
1,2-dichloroethane
R2 OH AcOH, 50 °C R2
TBAB, 65 °C
X
Sodium perborate in boron trifluoride etherate (1:5 mol ratio)
OH
has been found to be an effective reagent for the hydroperoxide
O B
HO O H
rearrangement of electron rich and highly substituted benzylic
HO
OO OH H+ 2 B O 2NaCl
+
B O
tertiary alcohols to phenols (eq 22).49 The reaction is incomplete
OH
OH
when the ratio of SPB to boron trifluoride etherate was 1:4 or 1:3,
even after 24 h.
X
R
OH
OH O
HX
H3BO3 +H2O2 HOX X2
R
NaBO3Å"4H2O
TBAB
BF3 Et2O, THF
R R
Sodium perborate and potassium bromide44 (or potassium
(22)
iodide45) in glacial acetic acid acetic anhydride, with sodium
OH
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-
R
tivated anilines using potassium bromide and ammonium molyb-
date (eq 19)46 as catalyst. The catalyst accelerates the rate of A variety of aryl acetates are selectively cleaved to the corre-
reaction but is not essential for obtaining good yields and high sponding phenols (eq 23)50 using SPB in methanol under mild
ć%
selectivities. 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 Decarbonylation of imidazo-2-yl and pyrid-2-ylpyruvic acids
occurs readily whereas alkyl acetates are found to be unreactive to give the corresponding acetic acids has been achieved using
under the reaction conditions. aqueous SPB at room temperature. It is proposed that intramolec-
ular hydrogen bonding, which inhibits conventional decarbonyl-
O
O
ation, facilitates epoxidation and subsequent decarboxylation of
NaBO3/MeOH
the enol tautomers (eq 27).55
ArO CH3 25 °C Ar OH + MeO CH3 (23)
H
O
N
O
N
Calix[4] crown-4-ether can be conveniently oxidized by sodium
perborate tetrahydrate in trifluoroacetic acid to afford the mono- O2N
O2N
CO2H
N CO2H
N
quinone (eq 24). Diamide calix[4] and diester calix[4] crown-
Me
Me
4-ethers are also oxidized using sodium perborate tetrahydrate
in trifluoroacetic acid to give the corresponding diquinones.51
H
H
O
O N
N
CO2
SPB
O
O2N
O2N
O
NaBO3Å"4H2O N
N
O
O Me
CF3COOH Me
O
OH OH
O
N
O
O
O CO2H (27)
H+
O2N
N
Me
(24)
O
OHO
O Baeyer Villiger Oxidation. Sodium perborate/formic acid
mixtures have found wide application in the formation of sim-
O
O
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-
Aldehydes and Ketones. Sodium perborate has been used
pletely regioselective in favor of the bridgehead-migrated isomer
to oxidize aldehydes to esters52 in the presence of a mineral acid
B. Transesterification of ²-keto esters with various alcohols
(such as 70% HClO4) using vanadium pentaoxide (V2O5) as cata-
has been carried out using SPB as a catalyst under neutral condi-
lyst in an alcoholic medium. The oxidation is carried out by adding
tions (eq 29).57 The effectiveness of the protocol is manifested in
70% HClO4 over a period of time to a mixture containing alde-
its selectivity toward ²-keto esters, whereas other esters are found
hyde, catalyst (V2O5), SPB, and alcohol. Sodium perborate/acetic
to be unreactive under these reaction conditions.
anhydride is very effective and highly selective for the oxidative
HOOC
HOOC
cleavage of acetals to their respective esters (eq 25).53
Cl
Cl
NaBO3Å"4H2O
(28)
O
O
NaBO3Å"4H2O/Ac2O HCOOH, 66% O
OR´
R (25) O
R
Na2CO3, C6H6, 55 °C B
O A
O
O O
O O
An efficient and convenient method has been developed for the
NaBO3
+ + OH
R1
conversion of 2-hydroxy phenyl ketoxime to 1,2-benzisoxazole-
OR1 R2 OH
OR2
Toluene/
2-oxide with SPB in glacial acetic acid under mild reaction con-
(29)
ditions (eq 26).54 Interestingly, when the reaction is carried out
under reflux, deoximation is observed.
Alkenes, Iodoarenes, and Boranes. A series of Ä…,²-unsatu-
R5
rated ketones has been treated with SPB in water and 1,4-dioxane
R4
NaBO3Å"4H2O O under microwave irradiation to produce Ä…,²-epoxy ketones in
good yields (eq 30).58 Sodium perborate, with potassium per-
N O
AcOH, 45 55 °C
R5 manganate as a catalyst, has been shown to be a novel reagent
R2
for the epoxidation of steroidal 5-enes with attack occurring pre-
R4 OH
R1 R
dominantly on the ²-face.59 Sodium perborate is also used for the
N
OH Julia asymmetric epoxidation of enones60 other than chalcones in
R2
R5
the presence of polyleucine as catalyst. Yields are excellent and
R1 R
R4 OH
NaBO3Å"4H2O good enantiomeric excess (ee) values are observed. Bromination
of alkenes with sodium bromide in the presence of SPB in acetic
AcOH, Reflux
O
R2
acid provided high yields of dibromoalkanes (eq 31).61 The re-
R1 R
action of the iodoarenes with SPB in acetic acid in the presence
(26) ć%
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 from Ä…,Ä…-dichlorotoluenes and trialkylboranes also utilized SPB
high yields (86 99%). Addition of triflic acid as a promoter causes in the workup for oxidative cleavage of the organoborane.68,69,70
a dramatic increase in the yield of (diacetoxyiodo)arenes in The same overall transformation can be affected using the corre-
reactions of iodoarenes with SPB. The presence of CF3SO3H sponding benzaldehyde trisyl-71 or tosylhydrazone72 as the source
(in stoichiometric quantities) in the reaction mixture consider- of the aryl moiety, with yields generally being superior in the trisyl
ably enhances the oxidizing activity. When CF3SO3H is replaced series (eq 36).
by concentrated H2SO4, the final yields of ArI(OAc)2 are not
BH3-THF, Cyclohexene
improved. The SPB HOAc system has also been used in the
THF, 0 °C, 1 h
HO
preparation of various chiral hypervalent iodine compounds
NaBO3Å"4H2O, H2O
(eq 33).63
O
THF, rt, 2 h (35)
O
80%
O O
R3 R3
NHTris
R4 MW 2 3 min, NaBO3Å"4H2O R4
N BR2
(30)
OH
O
H2O, 1,4-dioxane
R1 R2 Base
R1 R2
NaBO3Å"4H2O
R
R
R3B
H2O
Br
X X
X
(36)
COOH
COOH NaBO3Å"4H2O
NaBr, AcOH
Br
(31)
Related Reagents. Hydrogen Peroxide; Sodium Percarbonate
(SPC); meta-Chloroperbenzoic Acid (MCPBA).
I
I(OAc)2
NaBO3Å"4H2O, CF3COOH
R AcOH
(32)
+ R
3 8 h, 40 45 °C, 86 99%
1. McKillop, A.; Koyuncu, D.; Krief, A.; Dumont, W.; Renier, P.; Trabelsi,
M., Tetrahedron Lett. 1990, 31, 5007.
Et Et
2. McKillop, A.; Tarbin, J. A., Tetrahedron 1987, 43, 1753.
OMe OMe
3. Ding, X.; Ge, Y.; Teng, Z.; Fan, J., Yiyao Gongye 1987, 18, 193.
.
1. NaBO3Å"4H2O, AcOH
OH
I I 4. Page, G. O., Synth. Commun. 1993, 23, 765.
(33)
2. p-TosOH, CH3CN
OTos
5. McKillop, A.; Kemp, D., Tetrahedron 1989, 45, 3299.
55%
OMe OMe
6. Karunakaran, C.; Manimekalai, P., Tetrahedron 1991, 47, 8733.
Et Et
7. Shimazaki, M.; Takahashi, M.; Komatsu, H.; Ohta, A.; Kajii, K.;
Komada, Y., Synthesis 1992, 555.
A convenient approach has been developed for iodolactoni-
8. Kabalka, G. W.; Reddy, N. K.; Narayana, C., Synth. Commun. 1993, 23,
sation using iodobenzene as catalyst. The active reagent was gene-
543.
rated in situ with tetra-n-butylammonium iodide (TBAI) and a
9. Ohta, A.; Ohta, M., Synthesis 1985, 216.
hypervalent iodine reagent, diacetoxyiodobenzene (PIDA). PIDA,
10. Mehta, S. M.; Vakilwala, M. V., J. Am. Chem. Soc. 1952, 74, 563.
in turn, was generated in situ using a catalytic amount of iodoben-
11. Santurri, P.; Robbins, F.; Stubbings, R., Org. Synth., Coll. Vol. 1973, 5,
zene with sodium perborate monohydrate as the stoichiomet-
341.
ric oxidant. A variety of olefinic acids, including ´-pentenoic
12. Ogata, Y.; Shimizu, H., Bull. Chem. Soc. Jpn. 1979, 52, 635.
acids, ´-pentynoic acids, and ´-hexynoic acid, gave high yields of
13. Ding, X.; Teng, Z.; Ge, Y., Youji Huaxue 1989, 9, 257 (Chem. Abstr.
lactones. (eq 34).64
1990, 112, 35 351y).
14. Holt, D. A.; Levy, M. A.; Yen, H.-K.; Oh, H.-J.; Metcalf, B. W.; Wier,
O
P. J., Bioorg. Med. Chem. Lett. 1991, 1, 27.
I
R1
5 mol %
CO2H R1
15. Zajac, W. W., Jr.; Darcy, M. G.; Subong, A. P.; Buzby, J. H., Tetrahedron
R2 O (34)
Lett. 1989, 30, 6495.
R2 n-Bu4NI 1.1 equiv
R3 NaBO3Å"H2O 2 equiv 16. Olah, G. A.; Ramaiah, P.; Lee, C.-S.; Prakash, G. K. S., Synlett 1992,
I
AcOH 5 equiv 337.
R3
CH2Cl2, 40 °C
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,
Sodium perborate has been shown to be especially useful for
29, 2967.
oxidizing organoborane intermediates. Primary alcohols can be
19. Gupton, J. T.; Duranceau, S. J.; Miller, J. F.; Kosiba, M. L., Synth.
prepared selectively from terminal alkenes in the presence of Commun. 1988, 18, 937.
ketone and aldehyde groups by hydroboration followed by SPB
20. Reed, K. L.; Gupton, J. T.; McFarlane, K. L., Synth. Commun. 1989, 19,
2595.
oxidation.65 For example, 5-methylhex-5-en-2-one is converted
into 6-hydroxy-5-methylhexan-2-one (eq 35) using SPB follow- 21. Dehmlow, E. V.; Vehre, B., Nouv. J. Chim. 1989, 13, 117.
ing hydroboration with dicyclohexylborane formed in situ from 22. Reed, K. L.; Gupton, J. T.; Solarz, T. L., Synth. Commun. 1989, 19, 3579.
BH3 THF and cyclohexene. Terminal alkynes are similarly trans- 23. Rashid, A.; Read, G., J. Chem. Soc. (C) 1967, 1323.
formed into aldehydes.66 The same general approach has been
24. Muzart, J.; N Ait Ajjou, A., Synth. Commun. 1991, 21, 575.
used to prepare (+)-isopinocampheol stereospecifically from (+)-
25. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.;
Ä…-pinene in 92% overall yield.67 A route to alkyl aryl carbinols 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. 48. Jain, S. L.; Sharma, V. B.; Sain, B., Tetrahedron 2006, 62,
Abstr. 1990, 112, 76 519c). 6841.
27. Prakash, G. K. S.; Krass, N.; Wang, Q.; Olah, G. A., Synlett 1991, 39. 49. Kabalka, G. W.; Reddy, N. K.; Narayana, C., Tetrahedron Lett. 1993, 34,
7667.
28. Jammot, J.; Pascal, R.; Commeyras, A., Tetrahedron Lett. 1989, 30,
563. 50. Bandgar, B. P.; Uppalla, L. S.; Sadavarte, V. S.; V. Patil, S. V., New J.
Chem. 2002, 26, 1273.
29. Reed, K. L.; Gupton, J. T.; Solarz, T. L., Synth. Commun. 1990, 20,
563. 51. Chen, C.-F.; Zheng, Q.-Y.; Huang, Z.-T., Synthesis 1999, 69
30. Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M., Tetrahedron Lett. 1989, 52. Gopinath, R.; Barkakaty, B.; Talukdar, B.; Patel, B. K., J. Org. Chem.
30, 1483. 2003, 68, 2944.
31. Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M., J. Org. Chem. 1989, 53. Bhat, S.; Ramesha, A. R.; Chandrasekharan, S., Synlett 1995, 16, 329.
54, 5930.
54. Jadhav, V. K.; Deshmukh, A. P.; Wadagaonkar, P. P.; Salunkhe, M. M.,
32. Matteson, D. S.; Moody, R. J., J. Org. Chem. 1980, 45, 1091. Synth. Commun. 2000, 30, 1521.
33. Koyuncu, D.; McKillop, A.; McLaren, L., J. Chem. Res. (S) 1990, 55. Ramsden, C. A.; Sargent, B. J.; Wallett, C. D., Tetrahedron Lett. 1996,
21. 37, 1901.
34. Kenley, R. A.; Lee, G. C.; Winterle, J. S., J. Org. Chem. 1985, 50, 56. Okabayashi, N.; Mitamura, S. (Shinnittetsu Kagaku), Jpn. Kokai Tokkyo
40. Koho, JP 08127578; Chem. Abstr. 1996, 125, 142586.
35. Cristau, H.-J.; Torreilles, E.; Ginieys, J.-F., Heteroatom Chem. 1990, 1, 57. Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S., Chem. Lett. 2001, 894.
277.
58. Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F., J. Chem. Res. (S) 1998,
36. Cristau, H.-J.; Torreilles, E.; Ginieys, J.-F., J. Chem. Soc., Perkin Trans. 668.
2 1991, 13.
59. Hanson, J. R.; Terry, N.; Uyanik, C., J. Chem. Res. (S) 1998, 50.
37. Karunakaran, C.; Venkataramanan, R., Catal. Commun. 2006, 7,
60. Lasterra-Sgnchez, M. E.; Felfer, U.; Mayon, P.; Roberts, S. M.; Thornton,
236.
S. R.; Todd, C. J., J. Chem. Soc., Perkin Trans. 1 1996, 343.
38. Sharifi, A.; Mohsenzadeh, F.; Mojtahedi, M. M.; Saidi, M. R.; Balalaie,
61. Kabalka, G. W.; Yang, K.; Reddy, N. K.; Narayana, C., Synth. Commun.
B., Synth. Commun. 2001, 31, 431.
1998, 28, 925.
39. Nongkunsarn, P.; Ramsden, C. A., Tetrahedron Lett. 1993, 34, 6773.
62. Hossain, Md. D.; Kitamura, T., J. Org. Chem. 2005, 70, 6984.
40. Nongkunsarn, P.; Ramsden, C. A., Tetrahedron 1997, 53, 3805.
63. Wirth, T.; Hirt, U. H., Tetrahedron: Asymmetry 1997, 8, 23.
41. Maeda, M.; Sakuma, C.; Kawachi, S.; Tabei, K.; Kerim, A.; Kurihara,
64. Liu, H.; Tan, C.-H., Tetrahedron Lett. 2007, 48, 8220.
T.; Akihiro Ohta, A., J. Labelled Compd. Radiopharm. 1995, 36, 85.
65. Kabalka, G. W.; Yu, S.; Li, N.-S., Tetrahedron Lett. 1997, 38, 5455.
42. Begtrup, M.; Vedsł, P., J. Chem. Soc., Perkin Trans. 1 1995, 243.
66. Kabalka, G. W.; Yu, S.; Li, N.-S., Tetrahedron Lett. 1997, 38, 7681.
43. Deshmukh, A. P.; Padiya, K. J.; Jadhav, V. K.; Manikrao M.; Salunkhe,
67. Kabalka, G. W.; Maddox, J. T.; Shoup, T.; Bowers, K. R., Org. Synth.
M. M., J. Chem. Res. (S) 1998, 828.
1996, 73, 116.
44. Hanson, J. R.; Harpel, S.; Rodriguez Medina, I. C.; Rose, D., J. Chem.
68. Kabalka, G. W.; Li, N.-S.; Yu, S., Tetrahedron Lett. 1995, 36, 8545.
Res. (S) 1997, 432.
69. Li, N.-S.; Su, Y.; Kabalka, G. W., J. Organomet. Chem. 1997, 531, 101.
45. Beinker, P.; Hanson, J. R.; Meindl, N.; Rodriguez Medina, I. C., J.
70. Li, N.-S.; Su, Y.; Kabalka, G. W., Organometallics 1997, 16, 709.
Chem. Res. (S) 1998, 204.
71. Kabalka, G. W.; Maddox, J. T.; Bogas, E.; Tejedor, D.; Ross, E. J., Synth.
46. Roche, D.; Prasad, K.; Repic, O.; Blacklock, T. J., Tetrahedron Lett.
Commun. 1996, 26, 999.
2000, 41, 2083.
72. Kabalka, G. W.; Maddox, J. T.; Bogas, E.; Kelley, S. W., J. Org. Chem.
47. Jadhav, V. K.; Pal, R. R.; Wadgaonkar, P. P.; Salunkhe, M. M., Synth.
1997, 62, 3688.
Commun. 2001, 31, 3041.
A list of General Abbreviations appears on the front Endpapers