Hydroboration of fluoroolefins
Abstract
Reported herein is the development of the hydroboration of perfluoroalkyl(aryl) substituted alkenes. Pertinent highlights of the above stated methodology include (1) an absolute regioselective control of terminal fluorinated olefins by the judicious choice of organoborane reagent, (2) a facile synthesis of perfluoroalkyl vinyl iodides with a catalytic amount of zinc and trifluoroacetic acid and their appropriate palladium mediated cross-coupling reactions, (3) the investigation of highly electron-withdrawing perfluoroalkyl- and aryl entities upon a variety of substituted olefins, (4) absolute regio control of terminal perfluoroalkyl(aryl)ethylenes via an empirical selection of both rhodium catalyst and dialkoxyborane, and (5) the investigation of asymmetric hydroboration, both uncatalyzed and catalyzed, of fluorinated aliphatic and aromatic alkenes. Success in this area has opened the door for utilization of such methodology for the facile construction of potentially useful fluoroorganic intermediates.
Degree
Ph.D.
Advisors
Ramachandran, Purdue University.
Subject Area
Organic chemistry
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