Reaction of 2-hydroxybenzaldehydes with alkynes, alkenes, or allenes via cleavage of the aldehyde C-H bond using a rhodium catalyst system

被引：85

作者：

Kokubo, K ^{[1
]}

Matsumasa, K ^{[1
]}

Nishinaka, Y ^{[1
]}

Miura, M ^{[1
]}

Nomura, M ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 02期

关键词：

D O I：

10.1246/bcsj.72.303

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Hydroxybenzaldehydes smoothly and efficiently react with various internal and terminal alkynes accompanied by cleavage of the aldehyde C-H bond by using a rhodium-based catalyst system of [RhCl(cod)](2)/dppf/Na2CO3 [cod = 1,5-cyclooctadiene; dppf=1,1'-bis(diphenylphosphino)ferrocene] to give the corresponding 2-alkenoylphenols in good to excellent yields. The regioselectivity of the reaction depends on the substituents of acetylene; an oxygen function on the propargylic position shows a considerable directing effect. The aldehydes can also react with some alkenes or allenes, such as triethylvinylsilane and 2-norbornene or 3-methyl-1,2-butadiene and 1,2-nonadienes, in place of alkynes.

引用

页码：303 / 311

页数：9

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