Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

• Published in: Angewandte Chemie Vol. 128; no. 50; pp. 15773 - 15777
• Main Authors: Liu, Jiandong, Ren, Qinghua, Zhang, Xinghua, Gong, Hegui
• Format: Journal Article
• Language: English
• Published: Weinheim Blackwell Publishing Ltd 12.12.2016; Wiley Subscription Services, Inc
• Subjects: Alkene; Arene; Aromatic compounds; Bromides; Chemistry; Coupling; Displays; Halides; Kreuzkupplungen; Nickel; Pathways; Reaktionsmechanismen; Tolerances
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.201607959

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays good chemoselectivity between the two C(sp2)‐halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols. Ähnlich, doch nicht gleich: Eine nickelkatalysierte reduktive Kreuzkupplung von Elektrophilen verknüpft Arylhalogenide und Vinylbromide zu Vinylarenen. Da das Katalysatorsystem zwischen den beiden C(sp2)‐Halogeniden als Kupplungspartner unterscheidet, muss ein anderer Reaktionsmechanismus vorliegen als bei stufenweisen Umsetzungen.