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A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis
preprintsubmitted on 07.01.2021, 17:29 and posted on 08.01.2021, 13:04 by Zhonglin Liu, Lucas Oxtoby, Mingyu Liu, Zi-Qi Li, Van Tran, Yang Gao, Keary Engle
The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.
Combinatorial, Catalytic Functionalization of Alkenes and Alkynes
National Institute of General Medical SciencesFind out more...