Chemoselective hydroamination of vinyl arenes catalyzed by an NHC-amidate-alkoxide Pd(II) complex and p-TsOH

TETRAHEDRON LETTERS

卷:54

Article

Jung, Kyung Woon¹ 

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

关键词: Hydroamination;    Vinyl arenes;    Palladium catalyst;    Bronsted acid;    Sulfonamide;   

DOI  :  10.1016/j.tetlet.2013.05.101

来源: Elsevier

【 摘 要 】

The hydroamination of various substituted vinyl arenes with benzenesulfonamide was explored using an NHC-amidate-alkoxide palladium catalyst in conjunction with p-TsOH. Utilizing halide-substituted and electron-rich vinyl arenes, this methodology selectively furnished the cross-coupled hydroamination products in moderate to excellent yields in a Markovnikov fashion while greatly reducing undesired acid-catalyzed homocoupling of the vinyl arenes. Electron-rich vinyl arenes typically required milder conditions than electron-poor ones. While most effective for para-substituted substrates, the catalyst system also furnished the desired products from ortho- and meta-substituted vinyl arenes with high chemoselectivities. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free