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A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

preprint
submitted 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.

Funding

Combinatorial, Catalytic Functionalization of Alkenes and Alkynes

National Institute of General Medical Sciences

Find out more...

NSF-DGE-184247

RCSA (Cottrell Scholars Program)

Shanghai Institute of Organic Chemistry Postdoctoral Fellowship

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

United States

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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