Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 13, Pages 5149-5153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b01531
Keywords
-
Categories
Funding
- NSERC (Discovery Grant)
- NSERC (Canada Research Chairs programs)
- McLean Foundation
- University of Toronto
- Canada Foundation for Innovation [17545, 19119]
- Government of Ontario
- Centre for Advanced Computing (CAC) at Queen's University in Kingston, Ontario
- Canada Foundation for Innovation
- Queen's University
Ask authors/readers for more resources
Diphenylborinic acid serves as a cocatalyst for site- and stereoselective C-H alkylation reactions of carbohydrates under photoredox conditions using quinuclidine as the hydrogen atom transfer mediator. Products arising from selective abstraction of the equatorial hydrogens of cis-1,2-diol moieties, followed by C-C bond formation with net retention of configuration, are obtained. Computational modeling supports a mechanism involving formation of a tetracoordinate borinic ester, which accelerates hydrogen atom transfer with the quinuclidine-derived radical cation through polarity-matching and/or ion-pairing effects.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available