Divergent Synthesis of <scp><i>N</i>‐Heterocycles</scp> by Merging Borane‐Mediated Cyclopropane <scp>Ring‐Opening</scp> and Hydride Abstraction
Ziyu Zhang, Jie Ren, Ming Zhang, Xiufang Xu, Xiaochen Wang
Abstract
Main observation and conclusion Herein, we report the synthesis of N‐heterocycles by borane‐catalyzed dehydrogenative cyclization of 2‐cyclopropyl‐N,N‐dimethylanilines. Borane‐mediated cyclopropane ring‐opening and borane‐mediated hydride abstraction from an N‐methyl group are the key steps. The substituent at the cyclopropyl unit was found to greatly influence the reaction pathway and thus determined the major reaction product.
Topics & Concepts
ChemistryBoraneCyclopropaneHydrideSubstituentRing (chemistry)Medicinal chemistryStereochemistryCatalysisCombinatorial chemistryOrganic chemistryHydrogenCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis