Nickel-Catalyzed Regioselectivity-Switchable Hydroheteroarylation of Vinylarenes with Electron-Rich Heteroarenes

Yu Shui; Sajid Imran; Wen-Hui Jin; Yang Liu; Nadia Ismaeel; Hong-Mei Sun

doi:10.1021/acs.orglett.3c03618

Nickel-Catalyzed Regioselectivity-Switchable Hydroheteroarylation of Vinylarenes with Electron-Rich Heteroarenes

Org Lett. 2023 Dec 15;25(49):8866-8871. doi: 10.1021/acs.orglett.3c03618. Epub 2023 Dec 7.

Authors

Yu Shui¹, Sajid Imran¹, Wen-Hui Jin¹, Yang Liu¹, Nadia Ismaeel¹, Hong-Mei Sun¹

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

PMID: 38059777
DOI: 10.1021/acs.orglett.3c03618

Abstract

We report the first example of a regioselectivity switch in the hydroheteroarylation of vinylarenes with electron-rich heteroarenes, including benzofurans, benzothiophenes, and indoles, using an expedient ligand-controlled strategy. In the presence of NaO^tBu, Ni(IMes^Me)[P(OEt)₃]Br₂ yields C2-alkylated heteroarenes with high branched selectivity, whereas the use of Ni(IPr^*OMe)[P(OEt)₃]Br₂ favors the formation of the corresponding linear products. This robust method also provides easy access to a range of C2-alkylated electron-rich heteroarenes without employing directing groups.