Palladium-Catalyzed Heteroarylation and Concomitant ortho-Alkylation of Aryl Iodides
Dr. Chuanhu Lei
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorXiaojia Jin
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jianrong (Steve) Zhou
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)Search for more papers by this authorDr. Chuanhu Lei
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorXiaojia Jin
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jianrong (Steve) Zhou
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)Search for more papers by this authorGraphical Abstract
Three-in-one: The heteroarylation of aryl iodides and ortho-alkylation of the aryl rings occur in a single operation. The palladium and norbornene cocatalyst system effectively promoted the cleavage of two CH bonds and the formation of two new CC bonds, including a very hindered aryl–heteroaryl bond.
Abstract
Three-component couplings were achieved from common aryl halides, alkyl halides, and heteroarenes under palladium and norbornene co-catalysis. The reaction forges hindered aryl–heteroaryl bonds and introduces ortho-alkyl groups to aryl rings. Various heterocycles such as oxazoles, thiazoles and thiophenes underwent efficient coupling. The heteroarenes were deprotonated in situ by bases without the assistance of palladium catalysts.
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