TsNBr2 mediated oxidative functionalization of alkynes

被引：28

作者：

Rajbongshi, Kamal Krishna ^{[1
]}

Hazarika, Debojit ^{[1
]}

Phukan, Prodeep ^{[1
]}

机构：

[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India

来源：

TETRAHEDRON | 2016年 / 72卷 / 29期

关键词：

TsNBr2; Alkyne; Ketone; alpha-Bromoketone; 1-Bromoalkyne; HYPERVALENT IODINE REAGENT; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; CATALYZED HYDRATION; EFFICIENT SYNTHESIS; ALPHA-BROMOKETONES; REGIOSELECTIVE HYDRATION; SELECTIVE DEBROMINATION;

D O I：

10.1016/j.tet.2016.05.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2 mediated process. Alkynes could be readily converted to ketones and alpha-bromoketones via an oxybromination debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3 in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2 and Na2SO3 in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding alpha-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2 at room temperature. In all cases, excellent yields of corresponding products are obtained. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4151 / 4158

页数：8

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