Copper‐Catalyzed Aryne Insertion into the Carbon‐Iodine Bond of Heteroaryl Iodides

Author:

Cao Wen‐Xuan1,Zhu Lei1,He Yiyi1,Wang Run1,Liu Ming1,Ouyang Qin1,Xiao Qing1ORCID

Affiliation:

1. School of Pharmacy Third Military Medical University Gao Tanyan Avenue Chongqing 400038 China

Abstract

AbstractAryne 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.

Funder

National Natural Science Foundation of China

Key Technologies Research and Development Program

Natural Science Foundation of Chongqing Municipality

Publisher

Wiley

Subject

General Medicine

Reference88 articles.

1. For Kobayashi's generation of arynes fromo-silyltriflate precursors see:

2. FLUORIDE-INDUCED 1,2-ELIMINATION OFO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS

3. o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

4. For Hoye's generation of arynes from HDDA reactions see:

5. The hexadehydro-Diels–Alder reaction

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