Organic letters

DMF as Carbon Source: Rh-Catalyzed α-Methylation of Ketones

Y Li, D Xue, W Lu, C Wang, ZT Liu, J Xiao

Index: Li, Yang; Xue, Dong; Lu, Wei; Wang, Chao; Liu, Zhao-Tie; Xiao, Jianliang Organic Letters, 2014 , vol. 16, # 1 p. 66 - 69

Full Text: HTML

Citation Number: 29

Abstract

An unprecedented Rh-catalyzed direct methylation of ketones with N, N-dimethylformamide (DMF) is disclosed. The reaction shows a broad substrate scope, tolerating both aryl and alkyl ketones with various substituents. Mechanistic studies suggest that DMF delivers a methylene fragment followed by a hydride in the methylation process.

 Related Synthetic Route

~71%

~25%

~%

~%

~%

~64%

~62%

~64%

~72%

~69%

~59%

~43%

~%

~62%

~73%

~45%

~65%

~68%

~74%

~56%

~56%

~%

~70%

~44%

~%

~63%

~60%

~62%

~63%