硝酰自由基/PhI(OAc)2：邻二醇一锅法氧化裂解为（二）羧酸。

Nitroxyl radical/PhI(OAc)2: one-pot oxidative cleavage of vicinal diols to (di)carboxylic acids.

机构信息

Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan.

出版信息

Org Lett. 2012 Oct 5;14(19):5010-3. doi: 10.1021/ol3021435. Epub 2012 Sep 19.

DOI:10.1021/ol3021435

PMID:22991946

Abstract

A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)(2) is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.

摘要

本文描述了使用 AZADOs 和 PhI(OAc)(2)，温和且易于使用的一锅法将邻二醇氧化裂解为相应的（二）羧酸。1,2-二醇和 2,3-二醇以及 1,2,3-三醇生成了一至两个碳单元短的羧酸。内部邻二醇也能顺利地进行一锅氧化裂解，得到相应的二羧酸。环状邻二醇转化为相应的开环二羧酸。