Rhodium-Catalyzed Diverse Arylation of 2,5-Dihydrofuran: Controllable Divergent Synthesis via Four Pathways
Junhao Xing, Wanjiang Zhu, Bihai Ye, Tao Lu, Tamio Hayashi, Xiaowei Dou
Abstract
The rhodium-catalyzed controllable diverse arylation of 2,5-dihydrofuran with arylboronic acids is reported. By fine-tuning of the reaction conditions, four different ring-opening or oxidative arylation pathways are controlled in the rhodium-catalyzed arylation of 2,5-dihydrofuran, granting selective access to 2-aryl or 3-aryl homoallylic alcohols and 3-aryl or 4-aryl-2,3-dihydrofurans. The catalytic asymmetric ring-opening arylation of 2,5-dihydrofuran was also realized. Four plausible reaction pathways were proposed, based on the experimental results.
Topics & Concepts
RhodiumCatalysisArylChemistryRing (chemistry)Combinatorial chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms