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A mild method for the deborylation deuteration of arylboronic acids with DO, mediated by the synergistic combination of a thiol, a Lewis base, and photoredox catalysis, is reported. This reaction showed a broad substrate scope, excellent deuterium incorporation, and functional group tolerance. Therefore, this method is practical for the site-selective D-labeling of bioactive molecules and drug molecules.
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Arylboronic Acid Deborylation Deuteration via Synergistic Thiol, Lewis Base, and Photoredox Catalysis.
Org Lett
March 2022
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, College of Pharmacy, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, People's Republic of China.
A mild method for the deborylation deuteration of arylboronic acids with DO, mediated by the synergistic combination of a thiol, a Lewis base, and photoredox catalysis, is reported. This reaction showed a broad substrate scope, excellent deuterium incorporation, and functional group tolerance. Therefore, this method is practical for the site-selective D-labeling of bioactive molecules and drug molecules.
View Article and Find Full Text PDFHarnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization.
J Org Chem
August 2015
Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation.
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