Role of catechol in the radical reduction of B-alkylcatecholboranes in presence of methanol.
Mechanistic investigations on the previously reported reduction of B-alkylcatecholboranes in the presence of methanol led to the disclosure of a new mechanism involving catechol as a reducing agent. More than just revising the mechanism of this reaction, we disclose here the surprising role of catechol, a chain breaking antioxidant, which becomes a source of hydrogen atoms in an efficient radical chain process.
Povie
Guillaume
G
University of Berne, Department of Chemisty and Biochemistry, Freiestrasse 3, CH-3012 Berne, Switzerland.
Villa
Giorgio
G
Ford
Leigh
L
Pozzi
Davide
D
Schiesser
Carl H
CH
Renaud
Philippe
P
D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001880:Boranes; D002396:Catechols; D005609:Free Radicals; C034221:catechol; D000432:Methanol