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Suzuki−Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C. One-Pot Chemoselective Double Cross-Coupling Reactions†
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Abstract
The Suzuki−Miyaura cross-coupling of arenediazonium tetrafluoroborate salts with boronic acid partners catalyzed by Pd(0)/C is described as a practical and efficient alternative to classical homogeneous conditions. Reactions conducted in alcoholic solvents proved to be extremely fast using mild conditions. Additionnaly, we developed a chemoselective double Suzuki−Miyaura cross-coupling in a single reaction vessel allowing the synthesis of unsymmetrical terphenyls.
Citing Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
Unprecedented Substoichiometric Use of Hazardous Aryl Diazonium Salts in the Heck-Matsuda Reaction via a Double Catalytic Cycle
François Le Callonnec, Eric Fouquet, and François-Xavier FelpinOrganic Letters2011 Article ASAPUnprecedented Substoichiometric Use of Hazardous Aryl Diazonium Salts in the Heck-Matsuda Reaction via a Double Catalytic Cycle
François Le Callonnec, Eric Fouquet, and François-Xavier FelpinOrganic Letters2011 Article ASAPThe first Heck-Matsuda reaction using a catalytic amount of diazonium salts has been discovered. The reaction proceeds through an unprecedented double catalytic cycle in which the electrophile is in situ generated through the reaction advancement. This ...
Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals
Maria J. Climent, Avelino Corma, and Sara IborraChemical Reviews2011 111 (2), 1072-1133Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals
Maria J. Climent, Avelino Corma, and Sara IborraChemical Reviews2011 111 (2), 1072-1133
A New Route to Multifunctionalized p-Terphenyls and Heteroaryl Analogues via [5C + 1C(N)] Annulation Strategy
Lei Zhang, Fushun Liang, Xin Cheng and Qun LiuThe Journal of Organic Chemistry2009 74 (2), 899-902A New Route to Multifunctionalized p-Terphenyls and Heteroaryl Analogues via [5C + 1C(N)] Annulation Strategy
Lei Zhang, Fushun Liang, Xin Cheng and Qun LiuThe Journal of Organic Chemistry2009 74 (2), 899-902p-Terphenyls and heteroaryl analogues including bipyridines were prepared via [5C + 1C(N)] annulation of α-aryl-α-alkenoyl ketene-(S,S)-acetals (five carbon 1,5-bielectrophilic species) with nitroethane or ammonium acetate. The reaction features mild ...
Detonation Nanodiamond: An Organic Platform for the Suzuki Coupling of Organic Molecules
Weng Siang Yeap, Shiming Chen and Kian Ping LohLangmuir2009 25 (1), 185-191Detonation Nanodiamond: An Organic Platform for the Suzuki Coupling of Organic Molecules
Weng Siang Yeap, Shiming Chen and Kian Ping LohLangmuir2009 25 (1), 185-191Detonation nanodiamond possesses facile surface functional groups and can be chemically processed for many engineering applications. In this work, we demonstrate the functionalization of nanoscale diamond particles with aryl organics using Suzuki coupling ...
Pd-Catalyzed Efficient One-Pot Sequential Cross-Coupling Reactions of Aryl Dihalides
Xiaoming Zhang, Ailing Liu and Wanzhi ChenOrganic Letters2008 10 (17), 3849-3852Pd-Catalyzed Efficient One-Pot Sequential Cross-Coupling Reactions of Aryl Dihalides
Xiaoming Zhang, Ailing Liu and Wanzhi ChenOrganic Letters2008 10 (17), 3849-3852
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History
- Published In Issue July 19, 2007
- Received May 30, 2007
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