Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones

被引：57

作者：

Verma, Ajay ^{[1
]}

Kumar, Sangit ^{[1
]}

机构：

[1] IISER Bhopal, Dept Chem, Bhopal By Pass Rd, Bhopal 462066, Madhya Pradesh, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 17期

关键词：

ONE-POT SYNTHESIS; C-H BOND; COUPLING REACTIONS; GREEN CHEMISTRY; RADICAL PROCESS; ATOM ECONOMY; FUNCTIONALIZATION; ARYL; ARYLATION; 4H-3,1-BENZOXAZIN-4-ONES;

D O I：

10.1021/acs.orglett.6b02142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp(3))-C(sp(2)) bond employing iodine, sodium bicarbonate, and (t)butyl hydroperoxide in DMSO at 95 degrees C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.

引用

页码：4388 / 4391

页数：4

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