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Palladium/Silver Cocatalyzed Divergent Dimerization of 2<i>H</i>-Azirines for Regioselective Synthesis of Tetrasubstituted Pyrroles and Pyrimidines

Yongxing Zhao, Rui Li, Qingzheng Zhao, Jinzhong Yao, Maozhong Miao

2023Organic Letters19 citationsDOI

Abstract

-azirines have been developed under the catalysis of palladium and silver. Upon changing the reaction conditions, the fully aryl-substituted pyrrole and pyrimidine derivatives were furnished in moderate yields with regiospecificity, respectively. Control experiments uncovered distinct catalytic effects of two transition metals, and the proposed catalytic cycles plausibly rationalized the chemodivergence and regioselectivity.

Topics & Concepts

RegioselectivityChemistryPalladiumCatalysisPyrroleArylPyrimidineCombinatorial chemistryReaction conditionsOrganic chemistryMedicinal chemistryStereochemistryAlkylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms