Modified McFadyen–Stevens reaction for a versatile synthesis of aliphatic/aromatic aldehydes: design, optimization, and mechanistic investigations

…, R Takita, M Uchiyama, J Shimokawa, T Fukuyama

Index: Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119

Full Text: HTML

Citation Number: 3

Abstract

The traditional McFadyen–Stevens reaction requires harsh alkaline reaction conditions, thus precluding application to the synthesis of aliphatic aldehydes. Our modified McFadyen– Stevens reaction enables the transformation from the N, N-acylsulfonyl hydrazine to the corresponding aldehyde upon treatment with an imidazole–TMS imidazole combination without relying on oxidative or reductive reagents. The reduced basicity and in situ ...