- Direct syntheses of benzofuran-2(3H)-ones and benzofuran-3(2H)-ones from 1-(2-hydroxyphenyl)alkan-1-ones by CuBr2 or CuCl2
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New syntheses of benzofuran-2(3H)-ones and benzofuran-3(2H)-ones from 1-(2-hydroxyphenyl)alkan-1-ones via oxidative cyclization by CuBr2 or CuCl2 are described. A new synthesis of 1H-isochromene-1,4(3H)- diones via similar procedures is also described. Copyright
- Miyake, Hideyoshi,Nishimura, Akinori,Yago, Misato,Sasaki, Mitsuru
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- Reaction of 2-hydroxybenzaldehydes with alkynes, alkenes, or allenes via cleavage of the aldehyde C-H bond using a rhodium catalyst system
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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.
- Kokubo, Ken,Matsumasa, Kenji,Nishinaka, Yuko,Miura, Masahiro,Nomura, Masakatsu
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p. 303 - 311
(2007/10/03)
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