Rhodium-catalyzed direct ortho-alkenylation of phenyl sulfones with alkynes utilizing sulfonyl function as modifiable directing group

TETRAHEDRON

卷:71

Article

Nobushige, Kazunori¹  Hirano, Koji¹  Satoh, Tetsuya^1,2  Miura, Masahiro¹ 

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

[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan

关键词: Alkenylation;    C-H functionalization;    Rhodium;    Phenyl sulfone;   

DOI  :  10.1016/j.tet.2015.03.046

来源: Elsevier

【 摘 要 】

The ortho-selective alkenylation of phenyl sulfones with alkynes proceeds effectively in the presence of a cationic Cp*-rhodium(III) catalyst together with an appropriate carboxylic acid involving regioselective C-H bond cleavage directed by the sulfonyl function. An (ortho-alkenylated phenyl) methyl sulfone prepared by this hydroarylation method undergoes palladium-catalyzed alpha-arylation and subsequent diastereoselective cyclization to directly produce the corresponding thiochromane 1,1-dioxide derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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