TETRABUTYLAMMONIUM IODIDE 1

Tetrabutylammonium Iodide1 Ether Cleavage. Methyl, allyl, and benzyl ethers derived from
alcohols and phenols are regioselectively cleaved by a mixture of
Bu4 NI and a Lewis acid (Boron Trifluoride Etherate14 or Alu-
n-Bu4NI minum Iodide15 ).

[311-28-4] C16 H36 IN (MW 369.43) Alkyl and Vinyl Iodide. Bu4 NI can also be used as a source of
InChI = 1/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16- iodide for nucleophilic displacement reactions. Neopentyl iodides
12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1/fC16H36N.I/h;1h/ can be prepared via SN 2 displacement of the corresponding triflate
qm;-1 (eq 3).16 Alkenyliodonium tetrafluoroborates can be converted to
InChIKey = DPKBAXPHAYBPRL-ZKCUATCLCI vinyl iodides upon treatment with Bu4 NI (eqs 4 and 5).17

(phase-transfer catalyst;1 ether cleavage;1 alkyl iodide forma- SnBu3 Bu4NI SnBu3
tion;1 salt effects1 ) PhH
(3)
Physical Data: mp 148 ◦ C. CO2Me OTf
>84% CO2Me I
Solubility: sol EtOH, H2 O.
Form Supplied in: anhydrous white solid. I
Bu4NI
Analysis of Reagent Purity: tetraalkylammonium salts can be +
(4)
Ph IPh BF4–
titrated with potassium 3,5-di-t-butyl-2-hydroxybenzenesulfo- MeCN Ph
99%
nate and iron(III) chloride.1a (Z):(E) = 100:0
Purification: crystallize from toluene–petroleum ether, CH2 Cl2 –
petroleum ether (or hexane), acetone, ethyl acetate, EtOH–ethyl t-Bu + Bu4NI t-Bu
IPh BF4–
ether, aq EtOH, or H2 O. The solid is then dried at 90 ◦ C under I (5)
SO2Ph CH2Cl2 SO2Ph
high vacuum for 2 d.2 83%
Handling, Storage, and Precautions: highly hygroscopic solid. (Z):(E) = 100:0

Original Commentary
André B. Charette
Université de Montréal, Montréal, Québec, Canada First Update
Phase-transfer Catalyst. Although Bu4 NI is not as widely Petr Sazonov & Irina Beletskaya
used as Tetrabutylammonium Bromide, it is often used in phase- Moscow State University, Moscow, Russia
transfer reactions. It was shown to promote several N-alkylation
reactions3 of heterocycles such as pyrroles4 and of amides5,6 Transition-metal-catalyzed Cross Coupling. Bu4 NI
(eq 1). (though less frequently than Bu4 NBr) is used as an additive or
cocatalyst in cross-coupling reactions, often allowing use of less
active aryl bromides, chlorides, or sulfonates instead of costly
H2C=CHCH2Br
EtO2C N O EtO2C N O (1) aryl iodides.
H KOH, Bu4NI Bu4 NI was shown to accelerate and improve the selectivity of
43%
Ni-catalyzed cross coupling of various organozinc halides, in-
cluding AlkZnHal, with aryl and alkenyl iodides, triflates, and
nonaflates.18,19 Addition of 3 equiv of Bu4 NI (together with
It has also been used in phase-transfer carbene-mediated cyclo- 4-fluorostyrene) was crucial in effecting the cross coupling of
propanation reactions,7 metal-catalyzed carbonylation reactions AlkZnHal with primary alkyl halides (eq 6).19,20
of organic halides,8,9 and Wittig alkenation reactions.10
Several O-alkylation reactions11 were shown to proceed much Ni(acac)2 (10 mol %)
faster if Bu4 NI was added to the reaction mixture. One particu- RZnI + FG-(CH2)n-I FG-(CH2)n-R (6)
larly interesting case is the benzylation of diethyl tartrate in which F 20 mol %
addition of a catalytic amount of Bu4 NI was shown to be essential 48–82%
Bu4NI (3 equiv)
for obtaining high yield of the desired product (eq 2).12 THF/NMP 2:1
–5 to 0 °C, 4–30 h
O OH BnBr, NaH O OBn
Bu4NI, 18-crown-6
OEt OEt (2)
EtO
76%
EtO A similar effect of Bu4 NI (10 mol %) was found in the CuI -
OH O OBn O catalyzed reaction of Grignard reagents with benzylphospho-
nates.21 Addition of Bu4 NI also led to significant improvement
A mixture of Zinc Chloride and Bu4 NI catalyzes the synthesis in the reactions of polyfunctional arylcopper reagents with var-
of cyclic carbonates from oxiranes and carbon dioxide at rt and ious ArX and HetX (X=Br, Cl, F, OTs) catalyzed by Co(acac)2
atmospheric pressure.13 (eq 7).22–24

Avoid Skin Contact with All Reagents

2 TETRABUTYLAMMONIUM IODIDE

Cu(CN)MgCl
F O rt, 15 min R1
Co(acac)2 (7.5 mol %) X SnCl4, Bu4NI
+ DME:THF:DMPU 3:2:1 + RCHO
CH2Cl2, rt
Bu4NI (1 equiv)
R2 X=Cl, OMs
CN
F
R1 R1
20 mol % R R
CN
OH
+ . OH
(11)

R2 R2

(7)
O A SnI4 –Bu4 NI system was also employed for the Reformatsky-
type condensation of α-bromoketones with aldehydes.40
The allylation of aldehydes with allyltrichlorosilane in the pres-
ence of O-donor ligands, including its asymmetric version, is pro-
87 % foundly accelerated by Bu4 NI (eq 12). Bu4 NBr was found to be
less effective.41,42
Bu4 NI proved to be an essential additive in the successful coup-
ling of vinylsilanes and carbonylative coupling of vinylstannanes R3
SiCl3 (S)-BINAPO (10 mol %)
with aryl triflates catalyzed by Pd0 (eq 8).25,26 R2 + RCHO
i-Pr2NEt (5 equiv), Bu4NI (1.2 equiv)
CH2Cl2, rt
CsF R1
SiPh2Me Ar
Pd(PPh3)4 (5 mol %)
+ ArOTf OH R3
(8)
CuI (5 mol %)
F Bu4NI (0.8 equiv)
F
R
(12)
R1 R2
Bu4 NI increases the yield in the palladium-catalyzed car-
30–80% ee
bonylation of aryl bromides27 which was used in the synthe-
sis of [carbonyl-11 C] amides.28 The addition of Bu4 NI allowed
Heck arylation of styrene with unactivated (palladacycle catalyst, TiCl4 -promoted Baylis–Hillman Reaction. TBAI was found
130 ◦ C)29 and activated (pyrazolylphosphine ligand) aryl chlo- to be an important additive in the TiCl4 -promoted Baylis–Hillman
rides (eq 9).30 reaction between α,β-unsaturated (vinylic, acetylenic, and cyclo-
H propyl) carbonyl compounds and aldehydes.43–45 Bu4 NI works
N better than other Bu4 NX or Me2 S and can be sometimes used in
N catalytic amounts. Reaction is diastereoselective, and with alkenes
usually gives syn-adducts (eqs 13 and 14).46–50
Cl
Ph2P
Pd(OAc)2, NaOAc O O OH
TiCl4–Bu4NI
+ (9) + RCHO
130 °C, DMAc, 24 h (13)
R 1 R2 CH2Cl2
R1 R
Bu4NI (1.0 equiv) 45% –78 °C
O R2 I

Allylation of Carbonyl Compounds and Related Reactions. H TiCl4 (0.26 equiv)

SnHal2 /Bu4 NI-NaI (Hal=I, Br, Cl) system was used in γ-syn- COMe
+ Bu4NI (0.3 equiv)
diastereoselective Barbier-type allylation of aldehydes with allyl Ar O
CH2Cl2, rt
halides, alcohols, and mesylates (eq 10).31–33
OH O
SnI2 (2 equiv)
NaI (2 equiv) Ar Me (14)
OH
R R1 Bu4NI (0.2 equiv)
+ R′CHO Cl
DMI-H2O 20–60 °C R′ (10)
X
X=Cl, Br, OH R2
Ether and Ester Cleavage. Bu4 NI is a reagent for the dealky-
A similar reaction with propargyl halides or mesylates af- lation of alkyl sulfonates, sulfonium ions, and phosphonates. The
fords a mixture of propargylation and allenylation products.34,35 dealkylation usually proceeds with quantitative yields and is often
TinIV halides (Hal=Cl, I) can be used (in catalytic or stoichiomet- used in the synthesis of natural products.51–57 The combination
ric amounts) instead of SnX2 , and the SnHal4 –Bu4 NI system is of three reagents Bu4 NI, BF3 , and N,O-bis(trimethylsilyl) trifluo-
shown to be superior to SnI2 –Bu4 NI for the selective propargyla- roacetamide was shown to be critical for the complete deethylation
tion with 2-propynyl mesylates (eq 11).36–39 of CF2 P(O)(OEt)2 groups in an oligopeptide.58

A list of General Abbreviations appears on the front Endpapers

 TETRABUTYLAMMONIUM IODIDE 3

A combination of Bu4 NI with BCl3 is a generally applicable, Na O Bu4NI (10 mol %)

selective and operationally simple reagent for the cleavage of pri- R1 N S
+ H2O, rt, 48 h
mary alkyl aryl ethers at low temperatures (eq 15).59,60 R2 Cl O
Tos
N
F F (18)
Bu4NI (2.5 equiv)
R1
BCl3 (2.5 equiv) (15) R2
CH2Cl2, –78 °–0 °C, 2 h
H3CO OCH3 HO OH
In the Zn(OTf)2 -catalyzed alkylation of indoles, the added
Bu4 NI converted prenyl bromide to more active prenyl iodide,
Catalytic Bu4 NI facilitates cyclic ether and lactone cleavage improving the β-regioselectivity.86 Its effect in many other alky-
with 48% HBr under microwave irradiation conditions.61 lation reactions with RX (X  = I) may be supposed to be of a similar
nature.87–89 Alkylation and acylation of the pyrrole nitrogen (for
Phase-transfer Catalysis. In the past decade Bu4 NI has con- protection purposes) requires the presence of Bu4 NI to proceed to
tinued to be used as a phase-transfer catalyst in the alkylation of O, completion.90,91
N, C, S, Se, and P-centred nucleophiles.62–66 Of particular interest Bu4 NI promotes glycosidation reactions, where it is superior to
is its application in CO2 -fixation—the synthesis of mixed carbon- Bu4 NBr. It is used alone or in combination with 2,6-dialkylpyri-
ates, carbamates, and carbazates by a three-component reaction dinium salts or Ag2 CO3 (eq 19).92–95
of CO2 , alcohol(amine), and alkyl halide (eq 16).67–72

Bu-t
Bu4NI, Cs2CO3 O
R1XHn + CO2 + R2Hal (16)
DMF, 20–60 °C R2 NH+I–
R1Hn-1X O H OBn
XHn=OH, NH2, NHNH2 HO Bu4NI Bu-t
BnO H + ROH
BnO H OBn
4 Å molecular sieves
OP(OEt)2 CH2Cl2
H
These conditions are also applicable to solid-phase synthesis.73
The addition of Bu4 NI was essential in avoiding alkylation H OBn
HO
of amines in the synthesis of carbamates.70 A similar system
BnO H (19)
(Cs2 CO3 , Bu4 NI) was also employed for the synthesis of dithio- BnO H OBn
carbonates, dithiocarbamates, and phosphonodithioformates from H OR
CS2 as well as for the N-alkylation of carbamates.74–77 In the syn-
thesis of carbonates Cs2 CO3 can be replaced by K2 CO3 .78,79
Using Bu4 NI as a phase-transfer catalyst allows control of the Reaction of Bu4 NI with AgSCF3 allowed generation of the
regioselectivity of [MeO]− -promoted anionic cyclization of 1- unstable [SCF3 ]− anion for nucleophilic aromatic substitution
aryl-3-hexen-1,5-diynes resulting in the selective formation of reactions.96
biaryl products (eq 17).80 In the presence of Bu4 NI catalyst N-perfluoroalkylation of
sodium azole salts was peformed (eq 20).97
R

1. NaH
R 2. ClCF2CF2Cl
Bu4NI (2 equiv) (20)
N DMF, Bu4NI N
MeONa, MeOH, reflux
(17)
H CF2CF2Cl

CN CN
Related Reagents. Tetra-n-butylammonium Bromide;
Sodium Iodide; Lithium Iodide.

Miscellaneous. In many cases Bu4 NI is used as a source of

iodide anion that acts as a nucleophile toward carbon or other el-
ement centers. It is used to generate TMSI from TMSCl in situ 1. (a) Sjöberg, K., Aldrichim. Acta 1980, 13, 55. (b) Jones, R. A., Aldrichim.
in activated cyclopropane ring cleavage.81 Catalytic Bu4 NI ac- Acta 1976, 9, 35. (c) Weber, W. P.; Gokel, G. W. Phase Transfer Catalysis
tivates iodosobenzene in the oxidation of tetrahydroisoquinoline in Organic Synthesis; Springer: New York, 1977. (d) Starks, C. M.;
Liotta, C. Phase Transfer Catalysis; Academic: New York, 1978. (e)
alkaloids, conceivably via nucleophilic attack of iodide at iodoso
Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis; Verlag
groups.82 A 1:1 complex of Bu4 NI and NBS was suggested as a Chemie: Deerfield Beach, FL, 1980. (f) Loupy, A.; Tchoubar, B. Salt
selective oxidant of alcohols.83 Nucleophilic attack of iodide on Effects in Organic and Organometallic Chemistry; VCH: Weinheim,
the N–Cl group underlies the Bu4 NI catalysis in the aziridination 1992.
of alkenes with chloramine-T and in unsaturated N-chloramine 2. Perrin, D. D.; Armarego, W. L. Purification of Laboratory Chemicals;
cyclization (eq 18).84,85 3rd ed.; Pergamon: Oxford, 1988.

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4 TETRABUTYLAMMONIUM IODIDE

3. (a) Baldwin, J. E.; Au, A.; Christie, M.; Haber, S. B.; Hesson, D., J. Am. 40. Masuyama, Y.; Ohtsuka, M.; Kondo, A., Synlett 2006, 3346.
Chem. Soc. 1975, 97, 5957. (b) van Leusen, A. M.; Bouma, R. J.; Possel, 41. Short, J. D.; Attenoux, S.; Berrisford, D. J., Tetrahedron Lett. 1997, 38,
O., Tetrahedron Lett. 1975, 3487. 2351.
4. Gonzalez, C. R.; Greenhouse, R., Heterocycles 1985, 23, 1127. 42. Nakajima, M.; Kotani, S.; Ishizuka, T.; Hashimoto, S., Tetrahedron Lett.
5. Sato, R.; Senzaki, T.; Goto, T.; Saito, M., Bull. Chem. Soc. Jpn. 1986, 2005, 46, 157.
59, 2950. 43. Taniguchi, M.; Hino, T.; Kishi, Y., Tetrahedron Lett. 1986, 27, 4767.
6. Keusenkothen, P. F.; Smith, M. B., Synth. Commun. 1989, 19, 2859. 44. Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K., Org. Lett. 1999, 1, 1383.
7. Dehmlow, E. V.; Leffers, W., J. Organomet. Chem. 1985, 288, C41. 45. Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K.,
8. Lakshmi Kantam, M.; Prabhakar Reddy, N.; Choudary, B. M., Synth. Tetrahedron 2001, 57, 987.
Commun. 1990, 20, 2631. 46. Zhang, C.; Lu, X., Synthesis 1996, 586.
9. For reviews on applications of phase-transfer agents in the metal- 47. Wei, H.-X.; Gao, J. J.; Li, G., Tetrahedron Lett. 2001, 42, 9119.
catalyzed organic transformations, see: (a) Alper, H. Fundamental 48. Sagar, R.; Pant, C. S.; Pathak, R.; Shaw, A. K., Tetrahedron 2004, 60,
Research in Homogeneous Catalysis; Plenum: New York, 1984; Vol. 11399.
4, p 79. (b) Alper, H., Adv. Chem. Ser. 1987, 326, 8.
49. Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K., J. Org. Chem. 2001, 66,
10. Piechucki, C., Synthesis 1974, 869. 7854.
11. For a review of Bu4 NI-catalyzed reactions of O-tin ethers and 50. Shi, M.; Feng, Y.-S., J. Org. Chem. 2001, 66, 406.
stannylenes, see: David, S.; Hanessian, S., Tetrahedron 1985, 41, 643.
51. Johnson, D. C., II; Widlanski, T. S., Synthesis 2002, 809.
12. Nemoto, H.; Takamatsu, S.; Yamamoto, Y., J. Org. Chem. 1991, 56,
52. Xie, M.; Widlanski, T. S., Tetrahedron Lett. 1996, 37, 4443.
1321.
53. Park, C. E.; Jung, Y.-G.; Hong, J.-I., Tetrahedron Lett. 1998, 39, 2353.
13. Kisch, H.; Millini, R.; Wang, I.-J., Chem. Ber. 1986, 119, 1090.
54. Briggs, A. D.; Camplo, M.; Freeman, S.; Lundstrom, J.; Pring, B. G.,
14. Mandal, A. K.; Soni, N. R.; Ratnam, K. R., Synthesis 1985, 274.
Tetrahedron 1996, 52, 14937.
15. Andersson, S., Synthesis 1985, 437.
55. Gennari, C.; Longaria, C.; Ressela, S.; Saloma, B.; Mielgoa, A., Eur. J.
16. (a) Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G., J. Org. Chem. Org. Chem. 1998, 945.
1980, 45, 4387. (b) Harris, F. L.; Weiler, L., Tetrahedron Lett. 1987, 28,
56. Wirsching, J.; Voss, J., Eur. J. Org. Chem. 1999, 691.
2941.
57. Roush, W. R.; Gwaltney, S. L., II; Cheng, J.; Scheidt, K. A.; McKerrow,
17. (a) Ochiai, M.; Oshima, K.; Masaki, Y., J. Am. Chem. Soc. 1991, 113,
J. H.; Hansell, E., J. Am. Chem. Soc. 1998, 120, 10994.
7059. (b) Ochiai, M.; Oshima, K.; Masaki, Y., Tetrahedron Lett. 1991,
32, 7711. 58. Otaka, A.; Mitsuyama, E.; Kinoshita, T.; Tamamura, H.; Fujii, N., J. Org.
Chem. 2000, 65, 4888.
18. Jensen, A. E.; Dohle, W.; Knochel, P., Tetrahedron 2000, 56, 4197.
59. Brooks, P. R.; Wirtz, M. C.; Vetelino, M. G.; Rescek, D. M.; Woodworth,
19. Piber, M.; Jensen, A. E.; Rottlander, M.; Knochel, P., Org. Lett. 1999, 1,
G. F.; Morgan, B. P.; Coe, J. W., J. Org. Chem. 1999, 64, 9719.
1323.
60. Jarowicki, K.; Kocienski, P., J. Chem. Soc. Perkin Trans. 1 2000, 2495.
20. Jensen, A. E.; Knochel, P., J. Org. Chem. 2002, 67, 79.
61. Kad, G. L.; Kaur, I.; Bhandari, M.; Singh, J.; Kaur, J., Org. Process Res.
21. Kofink, C. C.; Knochel, P., Org. Lett. 2006, 8, 4121.
Dev. 2003, 7, 339.
22. Korn, T. J.; Schade, M. A.; Cheemala, M. N.; Wirth, S.; Guevara, S. A.;
62. Shieh, W.-C.; Dell, S.; Repic, O., Org. Lett. 2001, 3, 4279.
Cahiez, G.; Knochel, P., Synthesis 2006, 3547.
63. Conreaux, D.; Bossharth, E.; Monteiro, N.; Desbordes, P.; Balme, G.,
23. Korn, T. J.; Schade, M. A.; Wirth, S.; Knochel, P., Org. Lett. 2006, 8,
Tetrahedron Lett. 2005, 46, 7917.
725.
64. Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W., Tetrahedron Lett. 1999,
24. Korn, T. J.; Knochel, P., Angew. Chem., Int. Ed. 2005, 44, 2947.
40, 1843.
25. Hanamoto, T.; Kobayashi, T., J. Org. Chem. 2003, 68, 6354.
65. Cohen, R. J.; Fox, D. L.; Salvatore, R. N., J. Org. Chem. 2004, 69, 4265.
26. Hanamoto, T.; Handa, K.; Mido, T., Bull. Chem. Soc. Jpn. 2002, 75,
66. Cohen, R. J.; Fox, D. L.; Eubank, J. F.; Salvatore, R. N., Tetrahedron
2497.
Lett. 2003, 44, 8617.
27. Pri-Bar, I.; Alper, H., J. Org. Chem. 1989, 54, 36.
67. Chaturvedi, D.; Ray, S., Monatsh. Chem. 2006, 137, 127.
28. Karimi, F.; Langstrom, B., J. Chem. Soc. Perkin Trans. 1 2002, 2111.
68. Chu, F.; Dueno, E. E.; Jung, K. W., Tetrahedron Lett. 1999, 40, 1847.
29. Iyer, S.; Ramesh, C., Tetrahedron Lett. 2000, 41, 8981.
69. Fox, D. L.; Ruxer, J. T.; Oliver, J. M.; Alford, K. L.; Salvatore, R. N.,
30. Sun, Y.; Thiel, W. R., Inorg. Chim. Acta 2006, 359, 4807. Tetrahedron Lett. 2004, 45, 401.
31. Masuyama, Y.; Ito, A.; Kurusu, Y., Chem. Commun. 1998, 315. 70. Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.;
32. Masuyama, Y.; Ito, T.; Tachi, K.; Ito, A.; Kurusu, Y., Chem. Commun. Jung, K. W., Tetrahedron 2002, 58, 3329.
1999, 1261. 71. Salvatore, R. N.; Ledger, J. A.; Jung, K. W., Tetrahedron Lett. 2001, 42,
33. Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y., J. Org. Chem. 2000, 65, 6023.
494. 72. Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W., J. Org. Chem.
34. Masuyama, Y.; Ito, A.; Fukuzawa, M.; Terada, K.; Kurusu, Y., Chem. 2001, 66, 1035.
Commun. 1998, 2025. 73. Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W., Org. Lett. 2000,
35. Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y., Chem. Commun. 2000, 2, 2797.
2009. 74. Salvatore, R. N.; Sahab, S.; Jung, K. W., Tetrahedron Lett. 2001, 42,
36. Masuyama, Y.; Yamazuki, R.; Ohtsuka, M.; Kurusu, Y., Synlett 2006, 2055.
1750. 75. Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W., Tetrahedron
37. Masuyama, Y.; Takeuchi, K.; Kurusu, Y., Tetrahedron Lett. 2005, 46, Lett. 2001, 42, 1799.
2861. 76. Nagle, A. S.; Salvatore, R. N.; Cross, R. M.; Kapxhiu, E. A.; Sahab, S.;
38. Masuyama, Y.; Suga, T.; Watabe, A.; Kurusu, Y., Tetrahedron Lett. 2003, Yoon, C. H.; Jung, K. W., Tetrahedron Lett. 2003, 44, 5695.
44, 2845. 77. Fox, D. L.; Whitely, N. R.; Cohen, R. J.; Salvatore, R. N., Synlett 2003,
39. Masuyama, Y.; Watabe, A.; Kurusu, Y., Synlett 2003, 1713. 2037.

A list of General Abbreviations appears on the front Endpapers

 TETRABUTYLAMMONIUM IODIDE 5

78. Shi, M.; Shen, Y.-M., Molecules 2002, 7, 386. 89. Nam, J.; Chang, J.-Y.; Hahm, K.-S.; Park, Y. S., Tetrahedron Lett. 2003,
79. Chaturvedi, D.; Kumar, A.; Ray, S., Synth. Commun. 2002, 32, 2651. 44, 7727.
80. Wu, M.-J.; Lin, C.-F.; Lu, W.-D., J. Org. Chem. 2002, 67, 5907. 90. Handy, S. T.; Sabatini, J. J.; Zhang, Y.; Vulfova, I., Tetrahedron Lett.
81. Huang, H.; Forsyth, C. J., Tetrahedron 1997, 53, 16341. 2004, 45, 5057.
82. Huang, W.-J.; Singh, O. V.; Chen, C.-H.; Chiou, S.-Y.; Lee, S.-S., Helv. 91. Disingrini, T.; Muth, M.; Dallanoce, C.; Barocelli, E.; Bertoni, S.;
Chim. Acta 2002, 85, 1069. Kellershohn, K.; Mohr, K.; De Amici, M.; Holzgrabe, U., J. Med. Chem.
2006, 49, 366.
83. Beebe, T. R.; Boyd, L.; Fonkeng, S. B.; Horn, J.; Mooney, T. M.;
Saderholm, M. J.; Skidmore, M. V., J. Org. Chem. 1995, 60, 6602. 92. Hashimoto, S.; Honda, T.; Ikegami, S., Tetrahedron Lett. 1990, 31,
4769.
84. Wu, H.; Xu, L.-W.; Xia, C.-G.; Ge, J.; Yang, L., Synth. Commun. 2005,
35, 1413. 93. Tanaka, H.; Sakamoto, H.; Sano, A.; Nakamura, S.; Nakajima, M.;
Hashimoto, S., Chem. Commun. 1999, 1259.
85. Noack, M.; Gottlich, R., Eur. J. Org. Chem. 2002, 3171.
94. Garegg, P. J.; Maloisel, J.-L.; Oscarson, S., Synthesis 1995, 409.
86. Zhu, X.; Ganesan, A., J. Org. Chem. 2002, 67, 2705.
95. Sugimura, H.; Natsui, Y., Tetrahedron Lett. 2003, 44, 4729.
87. Brummond, K. M.; Hong, S.-P., J. Org. Chem. 2005, 70, 907.
96. Adams, D. J.; Clark, J. H., J. Org. Chem. 2000, 65, 1456.
88. Kim, H. J.; Chang, J.-Y.; Shin, E.-K.; Park, Y. S., Bull. Korean Chem.
Soc. 2005, 26, 273. 97. Petko, K.; Yagupolskii, L., Synth. Commun. 2006, 36, 1967.

Avoid Skin Contact with All Reagents