Palladium(II)-Catalyzed Markovnikov Hydroalkynylation of Unactivated Terminal Alkenes†
Chuanqi Hou
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Pinhong Chen
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Guosheng Liu
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
Chang-Kung Chuang Institute, East China Normal University, Shanghai, 200062 China
E-mail: [email protected]; [email protected]Search for more papers by this authorChuanqi Hou
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Pinhong Chen
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Guosheng Liu
State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China
Chang-Kung Chuang Institute, East China Normal University, Shanghai, 200062 China
E-mail: [email protected]; [email protected]Search for more papers by this authorDedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
Alkynes are versatile synthons in organic synthesis, as well as important structural moieties in bioactive molecules. Recently, transition metal-catalyzed hydroalkynylation of alkenes has been developed with reactive alkenes and alkenes bearing directing groups. However, the regioselective hydroalkynylation of simple alkenes is still challenging. Herein, we have developed a palladium-catalyzed Markovnikov hydroalkynylation of unactivated terminal alkenes, which provides an efficient approach for the synthesis of branched alkynyl compounds under mild conditions. This reaction features excellent functional group tolerance, good reaction yields and excellent regioselectivity. Moreover, the asymmetric hydroalkynylation reaction has also been achieved with moderate enantioselectivity by introducing a sterically bulky chiral Pyox ligand.
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