使用高价碘（lambda5）试剂与四乙基溴化铵结合，将α，α-二取代乙酰胺氧化转化为相应的少一个碳的酮。

Oxidative conversion of alpha,alpha-disubstituted acetamides to corresponding one-carbon-shorter ketones using hypervalent iodine (lambda5) reagents in combination with tetraethylammonium bromide.

机构信息

Department of Pharmaceutical Sciences & Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400 019, India.

出版信息

J Org Chem. 2008 Dec 5;73(23):9473-5. doi: 10.1021/jo801580g.

DOI:10.1021/jo801580g

PMID:18973384

Abstract

Alpha,alpha-disubstituted acetamides undergo oxidative dehomologation to give one-carbon-shorter ketones when reacted with a hypervalent iodine (lambda(5)) reagent in combination with tetraethylammonium bromide (TEAB) in various solvents. In further studies, one such combination of a hypervalent iodine (lambda(5)) reagent, o-iodoxybenzoic acid, and TEAB has been established as a new, mild, efficient, and general method for the transformation.

摘要

α,α-二取代乙酰胺与高价碘（λ(5)）试剂在各种溶剂中反应，并结合四乙基溴化铵（TEAB），会发生氧化去同系化反应，生成一个碳原子数更短的酮。在进一步的研究中，确定了高价碘（λ(5)）试剂邻碘酰苯甲酸与 TEAB 的这种组合是一种新的、温和、高效、通用的转化方法。