Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents. Academic Article uri icon

abstract

  • A highly chemoselective iron-catalyzed three-component dicarbofunctionalization of unactivated olefins with alkyl halides (iodides and bromides) and sp2-hybridized Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles (electron-rich and electron-deficient (hetero)aryl and alkenyl Grignard reagents), alkyl halides (tertiary alkyl iodides/bromides and perfluorinated bromides), and unactivated olefins bearing diverse functional groups including tethered alkenes, ethers, protected alcohols, aldehydes, and amines to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

published proceedings

  • Chem Sci

altmetric score

  • 11

author list (cited authors)

  • Liu, L., Lee, W., Youshaw, C. R., Yuan, M., Geherty, M. B., Zavalij, P. Y., & Gutierrez, O.

citation count

  • 21

complete list of authors

  • Liu, Lei||Lee, Wes||Youshaw, Cassandra R||Yuan, Mingbin||Geherty, Michael B||Zavalij, Peter Y||Gutierrez, Osvaldo

publication date

  • July 2020