Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
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 product...
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| Published in | Angewandte Chemie Vol. 128; no. 50; pp. 15773 - 15777 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Blackwell Publishing Ltd
12.12.2016
Wiley Subscription Services, Inc |
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| Abstract | 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. |
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| AbstractList | 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(sp super(2))-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.Original Abstract: Aehnlich, doch nicht gleich: Eine nickelkatalysierte reduktive Kreuzkupplung von Elektrophilen verknuepft Arylhalogenide und Vinylbromide zu Vinylarenen. Da das Katalysatorsystem zwischen den beiden C(sp super(2))-Halogeniden als Kupplungspartner unterscheidet, muss ein anderer Reaktionsmechanismus vorliegen als bei stufenweisen Umsetzungen. Abstract 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(sp 2 )‐halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols. 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. 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. |
| Author | Gong, Hegui Ren, Qinghua Liu, Jiandong Zhang, Xinghua |
| Author_xml | – sequence: 1 givenname: Jiandong surname: Liu fullname: Liu, Jiandong organization: School of Chemical and Environmental Engineering, Shanghai University of Technology, 100 Hai-Quan Road, 201418, Shanghai, China – sequence: 2 givenname: Qinghua surname: Ren fullname: Ren, Qinghua email: qinghua.ren@shu.edu.cn organization: Center for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, 200444, Shanghai, China – sequence: 3 givenname: Xinghua surname: Zhang fullname: Zhang, Xinghua email: xhzhang@sit.edu.cn organization: School of Chemical and Environmental Engineering, Shanghai University of Technology, 100 Hai-Quan Road, 201418, Shanghai, China – sequence: 4 givenname: Hegui surname: Gong fullname: Gong, Hegui email: hegui_gong@shu.edu.cn organization: Center for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, 200444, Shanghai, China |
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| Snippet | This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate... Abstract This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and... This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate... |
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| SubjectTerms | Alkene Arene Aromatic compounds Bromides Chemistry Coupling Displays Halides Kreuzkupplungen Nickel Pathways Reaktionsmechanismen Tolerances |
| Title | Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides |
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