Silver-Catalyzed 1,3-Aza-Benzyl Migration of Allyl Alcohol
Chuan‐Ming Hong, Si-Qi Xiong, Xue Zhang, Kai-Xian Ma, Qinghua Li, Tang‐Lin Liu
Abstract
Carbon migration of alkenyl alcohols has been recognized as an increasingly viable methodology in organic synthesis. Herein, we disclose a silver-catalyzed 1,3-aza-benzyl migration of allyl alcohols by utilizing chelation-assisted selective cleavage of an unstrained C(sp3)–C(sp3) bond. This approach provides an available, efficient, high atom-economic, and environmentally benign procedure, leading to alkylation products with broad substrate scopes and excellent yields. The migration proceeds via a one-pot, two-step process involving a free-state alkyl metal species.
Topics & Concepts
ChemistryCatalysisAlkylationCleavage (geology)AlkylBenzyl alcoholSubstrate (aquarium)ChelationBond cleavageCombinatorial chemistryAlcoholAtom economyMetalCarbon atomOrganic chemistryMedicinal chemistryEngineeringOceanographyGeotechnical engineeringFracture (geology)GeologyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis