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Oxygen and Base-Free Oxidative Heck Reactions of Arylboronic Acids with Olefins
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Abstract
A mild and efficient protocol for palladium-catalyzed oxidative Heck reactions of arylboronic acids with both electron-rich and -deficient olefins is described. In contrast to the normal oxidative Heck coupling, this new method works in the absence of a base, oxygen, or other external oxidants. With a wide variety of substrates tolerated, the method broadens the scope of palladium-catalyzed coupling reactions.
Citing Articles
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
Palladium-Catalyzed Oxidative Heck Coupling Reaction for Direct Synthesis of 4-Arylcoumarins Using Coumarins and Arylboronic Acids
Yaming Li, Zisong Qi, Huifeng Wang, Xinmei Fu, and Chunying DuanThe Journal of Organic Chemistry2012 Article ASAPPalladium-Catalyzed Oxidative Heck Coupling Reaction for Direct Synthesis of 4-Arylcoumarins Using Coumarins and Arylboronic Acids
Yaming Li, Zisong Qi, Huifeng Wang, Xinmei Fu, and Chunying DuanThe Journal of Organic Chemistry2012 Article ASAPAn efficient protocol for the direct synthesis of 4-arylcoumarins via palladium-catalyzed oxidative Heck coupling reaction of coumarins and arylboronic acids was developed. 4-Arylcoumarins were obtained in moderate to excellent yields, and the reaction ...
Pd-Catalyzed Olefination of Perfluoroarenes with Allyl Esters
Zejiang Li, Yuexia Zhang, and Zhong-Quan LiuOrganic Letters2012 14 (1), 74-77Pd-Catalyzed Olefination of Perfluoroarenes with Allyl Esters
Zejiang Li, Yuexia Zhang, and Zhong-Quan LiuOrganic Letters2012 14 (1), 74-77An efficient Pd(II)-catalyzed direct olefination of perfluoroarenes with allyl esters is demonstrated. Under the typical conditions, the coupling reaction of fluorinated-arenes with allylic esters proceeded via a β-H elimination rather than a β-OAc ...
Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of Mycobacterium tuberculosis 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase Inhibitors
Anneli Nordqvist, Christofer Björkelid, Mounir Andaloussi, Anna M. Jansson, Sherry L. Mowbray, Anders Karlén, and Mats LarhedThe Journal of Organic Chemistry2011 76 (21), 8986-8998Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of Mycobacterium tuberculosis 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase Inhibitors
Anneli Nordqvist, Christofer Björkelid, Mounir Andaloussi, Anna M. Jansson, Sherry L. Mowbray, Anders Karlén, and Mats LarhedThe Journal of Organic Chemistry2011 76 (21), 8986-8998Cinnamaldehyde derivatives were synthesized in good to excellent yields in one step by a mild and selective, base-free palladium(II)-catalyzed oxidative Heck reaction starting from acrolein and various arylboronic acids. Prepared α,β-unsaturated aldehydes ...
Pd-Catalyzed C4-Olefination of Oxazoles via C–H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives
Sunliang Cui, Lukasz Wojtas, and Jon C. AntillaOrganic Letters2011 13 (19), 5040-5043Pd-Catalyzed C4-Olefination of Oxazoles via C–H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives
Sunliang Cui, Lukasz Wojtas, and Jon C. AntillaOrganic Letters2011 13 (19), 5040-5043A Pd-catalyzed C4-olefination of oxazoles via C–H bond activation under mild conditions was achieved. The reaction was shown to be general over a range of substrates. New protocols for the divergent transformation of these products to provide ...
From α-Arylation of Olefins to Acylation with Aldehydes: A Journey in Regiocontrol of the Heck Reaction
Jiwu Ruan and Jianliang XiaoAccounts of Chemical Research2011 Article ASAPFrom α-Arylation of Olefins to Acylation with Aldehydes: A Journey in Regiocontrol of the Heck Reaction
Jiwu Ruan and Jianliang XiaoAccounts of Chemical Research2011 Article ASAPThe Pd-catalyzed Mizoroki–Heck reaction of olefins with aryl halides, more often simply called the Heck reaction, was recently recognized with the 2010 Nobel Prize in chemistry. Although highly selective with electron-deficient olefins, which generally ...
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History
- Published In Issue February 27, 2008
- Received October 30, 2007
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