Ken Kokubo, Kenji Matsumasa, Y. Nishinaka
Feb 1, 1999
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0
Influential Citations
79
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Journal
Bulletin of the Chemical Society of Japan
Abstract
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.