Practical iridium-catalyzed direct α-arylation of N-heteroarenes with (hetero)arylboronic acids by H2O-mediated H2 evolution

Liang Cao, He Zhao, Rongqing Guan, Huanfeng Jiang, Pierre. H. Dixneuf and Min Zhang ()
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Liang Cao: South China University of Technology
He Zhao: South China University of Technology
Rongqing Guan: South China University of Technology
Huanfeng Jiang: South China University of Technology
Pierre. H. Dixneuf: University of Rennes, ISCR
Min Zhang: South China University of Technology

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Despite the widespread applications of 2-(hetero)aryl N-heteroarenes in numerous fields of science and technology, universal access to such compounds is hampered due to the lack of a general method for their synthesis. Herein, by a H2O-mediated H2-evolution cross-coupling strategy, we report an iridium(III)-catalyzed facile method to direct α-arylation of N-heteroarenes with both aryl and heteroaryl boronic acids, proceeding with broad substrate scope and excellent functional compatibility, oxidant and reductant-free conditions, operational simplicity, easy scalability, and no need for prefunctionalization of N-heteroarenes. This method is applicable for structural modification of biomedical molecules, and offers a practical route for direct access to 2-(hetero)aryl N-heteroarenes, a class of potential cyclometalated C^N ligands and N^N bidentate ligands that are difficult to prepare with the existing α-C-H arylation methods, thus filling an important gap in the capabilities of synthetic organic chemistry.

Date: 2021
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DOI: 10.1038/s41467-021-24468-z

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