Copper-Catalyzed Aryne Insertion into the Carbon-Iodine Bond of Heteroaryl Iodides
Wen-Xuan Cao1, Lei Zhu1, Yiyi He1
1School of Pharmacy, Third Military Medical University, Gao Tanyan Avenue, Chongqing, 400038, China.
Abstract:
Aryne insertions into the carbon-iodine bond of heteroaryl iodides has been achieved for the first time. This novel reaction provides an efficient pathway for the synthesis of valuable building blocks 2-iodoheterobiaryls from heteroaryl iodides and o-silylaryl triflates in excellent regioselectivity. The copper(I) catalyst, which bears a N-heterocyclic carbene (NHC) ligand, is essential to accomplish the reaction. Control reactions and DFT calculations indicate that the coordination of copper, as a Lewis acid, with nitrogen atoms of heteroaryl iodides mediates the insertion of arynes into heteroaryl carbon-iodine bonds.
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