Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes. Academic Article uri icon

abstract

  • 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(sp2)-C(sp3) 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.

published proceedings

  • Chem Sci

altmetric score

  • 9.35

author list (cited authors)

  • Liu, L., Lee, W., Yuan, M., Acha, C., Geherty, M. B., Williams, B., & Gutierrez, O.

citation count

  • 20

complete list of authors

  • Liu, Lei||Lee, Wes||Yuan, Mingbin||Acha, Chris||Geherty, Michael B||Williams, Brandon||Gutierrez, Osvaldo

publication date

  • February 2020