Fe-Catalyzed C-C Bond Construction from Olefins via Radicals

Julian C. Lo, Dongyoung Kim, Chung Mao Pan, Jacob T. Edwards, Yuki Yabe, Jinghan Gui, Tian Qin, Sara Gutiérrez, Jessica Giacoboni, Myles W. Smith, Patrick L. Holland, Phil S. Baran

Research output: Contribution to journalArticle

125 Scopus citations

Abstract

This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor and acceptor olefins. Although the substitution on the donor olefins was initially limited to alkyl and aryl groups, additional efforts culminated in the expansion of the scope of the substitution to various heteroatom-based functionalities, providing a unified olefin reactivity. A vinyl sulfone acceptor olefin was developed, which allowed for the efficient synthesis of sulfone adducts that could be used as branch points for further diversification. Moreover, this reactivity was extended into an olefin-based Minisci reaction to functionalize heterocyclic scaffolds. Finally, mechanistic studies resulted in a more thorough understanding of the reaction, giving rise to the development of a more efficient second-generation set of olefin cross-coupling conditions.

Original languageEnglish (US)
Pages (from-to)2484-2503
Number of pages20
JournalJournal of the American Chemical Society
Volume139
Issue number6
DOIs
StatePublished - Feb 15 2017
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Lo, J. C., Kim, D., Pan, C. M., Edwards, J. T., Yabe, Y., Gui, J., Qin, T., Gutiérrez, S., Giacoboni, J., Smith, M. W., Holland, P. L., & Baran, P. S. (2017). Fe-Catalyzed C-C Bond Construction from Olefins via Radicals. Journal of the American Chemical Society, 139(6), 2484-2503. https://doi.org/10.1021/jacs.6b13155