Tetrahedron

Mild and selective deprotection of carbamates with Bu 4 NF

U Jacquemard, V Bénéteau, M Lefoix, S Routier…

Index: Jacquemard, Ulrich; Beneteau, Valerie; Lefoix, Myriam; Routier, Sylvain; Merour, Jean-Yves; Coudert, Gerard Tetrahedron, 2004 , vol. 60, # 44 p. 10039 - 10047

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Citation Number: 88

Abstract

A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated.

~99%

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~83%

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~97%

~66%

~17%

~16%

~21%

~87%

~85%

~99%

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