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Article Abstract
Herein copper-catalyzed Markovnikov protoborylation of unactivated terminal alkenes was achieved through the employment of a bulky σ-donating guanidine ligand. The reaction demonstrated good tolerance to diverse functional groups and remarkable selectivity for branched borylation products (86:14-97:3) under ambient conditions, which enabled the synthesis of secondary alkyl boronates in grams with further valuable derivatizations. Mechanistic studies suggested the boryl insertion to C═C bonds via Cu-guanidine complex and ruled out the possibility of a diboration-protodeboronation process.
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Markovnikov Protoborylation of Unactivated Terminal Alkenes via Copper-Guanidine Catalysis.
J Org Chem
June 2025
College of Materials, Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu, Sichuan 610059, P. R. China.
Herein copper-catalyzed Markovnikov protoborylation of unactivated terminal alkenes was achieved through the employment of a bulky σ-donating guanidine ligand. The reaction demonstrated good tolerance to diverse functional groups and remarkable selectivity for branched borylation products (86:14-97:3) under ambient conditions, which enabled the synthesis of secondary alkyl boronates in grams with further valuable derivatizations. Mechanistic studies suggested the boryl insertion to C═C bonds via Cu-guanidine complex and ruled out the possibility of a diboration-protodeboronation process.
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