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 Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 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 NaOtBu, Ni(IMesMe)[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.
链接： //pubs.acs.org/doi/10.1021/acs.orglett.3c03618
