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Title: Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes
Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of alkyl radical intermediates out of the solvent cage to participate in an intra- or intermolecular radical cascade with a range of VCPs followed by re-entering the Fe radical cross-coupling cycle to undergo (stereo)selective C(sp 2 )–C(sp 3 ) bond formation. This work provides a proof-of-concept of the use of vinyl cyclopropanes as synthetically useful 1,5-synthons in Fe-catalyzed conjunctive cross-couplings with alkyl halides and aryl/vinyl Grignard reagents. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.  more » « less
Award ID(s):
1751568
PAR ID:
10214127
Author(s) / Creator(s):
; ; ; ; ; ;
Date Published:
Journal Name:
Chemical Science
Volume:
11
Issue:
12
ISSN:
2041-6520
Page Range / eLocation ID:
3146 to 3151
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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