Palladium-Catalyzed Cross-Coupling of Ynones with Aryl Bromides Enabled by C(O)-C(sp) Bond Activation

IF 3.3 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Yanqiong Zhang, Qinyue Tao, Qiang Li, Zewei Jin, Dr. Yang Long, Prof. Dr. Xiangge Zhou
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Abstract

Transition metal-catalyzed cross-coupling reactions have emerged as one of the most attractive methods in organic synthesis in recent years. However, due to the inertness of C−C bonds, C−C bond activation enabled cross-coupling reactions are far less common. In this work, the first example of palladium-catalyzed cross-coupling of ynones with aryl bromides for the synthesis of diarylacetylenes via C(O)-C(sp) bond activation was described. The reaction exhibited directing group-free unstrained C−C bond activation, wide substrate scope, and good functional group tolerance. Preliminary mechanistic studies suggested that a cross-electrophile coupling reaction pathway might be involved rather than the conventional nucleophilic addition/β-C elimination pathway.

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C(O)-C(sp)键活化钯催化炔酮与芳基溴的交叉偶联。
过渡金属催化的交叉偶联反应是近年来有机合成中最具吸引力的方法之一。然而,由于C-C键的惰性,C-C键激活的交叉偶联反应远不常见。在这项工作中,钯-过渡金属催化的交叉偶联反应成为近年来有机合成中最具吸引力的方法之一。然而,由于C-C键的惰性,C-C键激活的交叉偶联反应远不常见。本文报道了钯催化壬酮与芳基溴交叉偶联,通过C(O)-C(sp)键活化合成二芳基乙炔的第一例。该反应具有定向无基无应变C-C键活化、底物范围广、官能团耐受性好等特点。初步的机理研究表明,与传统的亲核加成/β-C消除途径不同,可能涉及亲电偶联反应途径。介绍了用C(O)-C(sp)键活化法催化炔酮与芳基溴交叉偶联合成二芳基乙炔的方法。该反应具有定向无基无应变C-C键活化、底物范围广、官能团耐受性好等特点。初步的机理研究表明,与传统的亲核加成/β-C消除途径不同,可能涉及亲电偶联反应途径。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Chemistry - An Asian Journal
Chemistry - An Asian Journal 化学-化学综合
CiteScore
7.00
自引率
2.40%
发文量
535
审稿时长
1.3 months
期刊介绍: Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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