Visible-Light-Induced In Situ Generation of Fischer-Type Copper Carbene Complexes from Acylsilanes and Its Application to Catalytic [4+1] Cycloaddition with Siloxydienes

被引：30

作者：

Takeuchi, Taiichi ^{[1
]}

Aoyama, Tsukasa ^{[1
]}

Orihara, Kurumi ^{[1
]}

Ishida, Kento ^{[1
]}

Kusama, Hiroyuki ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Tokyo 1718588, Japan

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

关键词：

LATE TRANSITION-METALS; MECHANISTIC PHOTOCHEMISTRY; REGIOSELECTIVE SYNTHESIS; SELF-DIMERIZATION; 3+2 CYCLIZATION; TRANSMETALATION; DERIVATIVES; BENZOYLTRIMETHYLSILANE; SILYLACYLATIONS; SILOXYCARBENES;

D O I：

10.1021/acs.orglett.1c03683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology for in situ generation of Fischer-type metal-carbene complexes was developed. Photoirradiation to a mixture of an acylsilane and a cationic copper complex cleanly gave a Fischer-type copper-siloxycarbene complex, which was detected by spectroscopic methods. This carbene complex reacted with siloxydienes in a [4 + 1] cycloaddition manner to give cyclopentene derivatives. It is noteworthy that this reaction proceeds with a catalytic amount of copper through in situ generation of a Fischer-type copper-siloxycarbene complex intermediate.

引用

页码：9490 / 9494

页数：5