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Rhodaelectro‐Catalyzed <i>peri</i> ‐Selective Direct Alkenylations with Weak <i>O</i> ‐Coordination Enabled by the Hydrogen Evolution Reaction (HER)

Bartłomiej Sadowski, Binbin Yuan, Zhipeng Lin, Lutz Ackermann

2022Angewandte Chemie International Edition35 citationsDOIOpen Access PDF

Abstract

)-directing groups. In sharp contrast, direct electrocatalytic transformations of weakly-coordinating phenols remain underdeveloped. Herein, electrooxidative peri C-H alkenylations of challenging 1-naphthols were achieved by versatile rhodium(III) catalysis via user-friendly constant current electrolysis. The rhodaelectrocatalysis employed readily-available alkenes and a protic reaction medium and features ample scope, good functional group tolerance and high site- and stereoselectivity. The strategy was successfully applied to high-value, nitrogen-containing heterocycles, thereby providing direct access to uncommon heterocyclic motifs based on the dihydropyranoquinoline skeleton.

Topics & Concepts

CatalysisHydrogenChemistryOrganic chemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions