Copper-Catalyzed Silylation of C(sp3)-H Bonds Adjacent to Amide Nitrogen Atoms

被引：26
作者：
Feng, Jian-Jun [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 14期
关键词：
ENANTIOSELECTIVE ADDITION; NUCLEOPHILIC SILICON; RADICAL CYCLIZATION; ROOM-TEMPERATURE; N-CHLOROAMINES; REAGENTS; SILYLBORANES; ACTIVATION; OXIDATION; AMINATION;
D O I：
10.1021/acs.orglett.8b01698
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed C-Si bond formation between N-halogenated amides and Si-B reagents is described. This oxidative coupling enables the silylation of C(sp(3))-H bonds alpha to an amide nitrogen atom. The utility of the new method is demonstrated for sulfonamides, and N-chlorination with tBuOCl and C-H silylation employing CuSCN/4,4'-dimethoxy-2,2'-bipyridine as catalyst can be performed without purification of the N-Cl intermediate.
引用
收藏
页码：4273 / 4276
页数：4
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