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

Shui, Yu; Imran, Sajid; Jin, Wen-Hui; Liu, Yang; Ismaeel, Nadia; Sun, Hong-Mei*(孙宏枚)

¹Key Laboratoryof Organic Synthesisof JiangsuProvince,College of Chemistry,ChemicalEngineeringandMaterialsScience, SoochowUniversity,Suzhou 215123,China

Org.Lett.2023,25, 8866−8871

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]Br₂yields C2-alkylated heteroarenes with high branched selectivity, whereas the use of Ni(IPr*^OMe)[P(OEt)₃]Br₂favors 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.

链接：https://pubs.acs.org/doi/10.1021/acs.orglett.3c03618