Open AccessA Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis
Author(s) -
Zhonglin Liu,
Lucas J. Oxtoby,
Mingyu Li,
Ziqi Li,
Van Tan Tran,
Yang Gao,
Keary M. Engle
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c03178
Subject(s) - chemistry , vicinal , stereocenter , enantioselective synthesis , hexafluorophosphate , palladium , combinatorial chemistry , group (periodic table) , selectivity , catalysis , organic chemistry , ionic liquid
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.