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Photo-mediated synthesis of halogenated spiro[4,5]trienones of N-aryl alkynamides with PhI(OCOCF3)2 and KBr/KCl.
Liu, Tong; Li, Yaming; Jiang, Linlin; Wang, Jiaao; Jin, Kun; Zhang, Rong; Duan, Chunying.
Afiliação
  • Liu T; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Li Y; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Jiang L; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Wang J; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Jin K; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Zhang R; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
  • Duan C; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P.R. China. ymli@dlut.edu.cn.
Org Biomol Chem ; 18(10): 1933-1939, 2020 03 14.
Article em En | MEDLINE | ID: mdl-32101242
ABSTRACT
A novel and convenient photo-mediated halogenated spirocyclization of N-(p-methoxyaryl)propiolamides has been developed. The photolysis of phenyliodine bis(trifluoroacetate) (PIFA) as an iodination reagent led to iodinated ipso-cyclization under the irradiation of a xenon lamp, while brominated ipso-cyclization or chlorinated ipso-cyclization was achieved by irradiating a mixture of PIFA and KBr/KCl under a blue LED. The present protocol simply utilizes light as the safe and clean energy source and doesn't require any external photocatalyst providing various 3-halospiro[4,5]trienones in good to excellent yields (up to 93%).
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article