Nickel-Catalyzed Intermolecular Branched/Linear Regioselective C-H Alkylation of 4-Oxoquinazolines

A Ni−NHC-catalyzed prototype reaction based on the alkylation of C−H activated 4-oxoquinazolines with aryl and alkyl alkenes was demonstrated. When aryl alkenes are used as the substrates, the regioselection of the reaction can be fine-tuned by choosing a NHC ligand with appropriate steric hindrance to harvest branched adducts, while the use of a bulky NHC/alkyl aluminum cocatalyst system helps to steer the reaction towards linear products. For alkyl alkene substrates, Ni(cod)2, IMes ⋅ HCl and NaOtBu system can directionally generate linear products, and long-chain olefins are also applicable. In addition, the catalytic mechanism was also explored through the deuteration experiments, and the migration of nickel was suggested in the catalytic cycle. (Figure presented.). © 2023 Wiley-VCH GmbH.