Palladium-Catalyzed Markovnikov Terminal Arylalkynes Hydrostannation: Application to the Synthesis of 1,1-Diarylethylenes

被引：57

作者：

Hamze, Abdallah ^{[1
]}

Veau, Damien ^{[1
]}

Provot, Olivier ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

机构：

[1] Univ Paris Sud, Fac Pharm, Chim Therapeut Lab, CNRS,BioCIS,UMR 8076, F-92296 Chatenay Malabry, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

CINE-SUBSTITUTION; STILLE REACTION; NEOCARZINOSTATIN CHROMOPHORE; TRIBUTYLTIN HYDRIDE; ALKYNES; HYDROSILYLATION; LIGANDS; HYDROSTANNYLATION; VINYLSTANNANES; REGIOCONTROL;

D O I：

10.1021/jo802460z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed hydrostannation of terminal arylalkynes was achieved. The regioselectivity of the H-Sn bond addition across the triple bond was found to be controlled by an ortho substituent on the aromatic ring, whatever its electronic nature, to give exclusively alpha-branched vinylstannanes 2 in accordance with Markovnikov's rule. Subsequent Stille cross-coupling reaction of 2 with a variety of aryl halides readily provided, in moderate to good yields, a family of functionalized 1,1-diarylethylenes 1.

引用

页码：1337 / 1340

页数：4

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[2]

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[3]

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