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

被引：55
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
收藏
页码：4388 / 4391
页数：4
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