Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents. Issue 31 (31st July 2020)

• Record Type: Journal Article
• Authors: Liu, Lei; Lee, Wes; Youshaw, Cassandra R.; Yuan, Mingbin; Geherty, Michael B.; Zavalij, Peter Y.; Gutierrez, Osvaldo
• Is Part Of: Chemical science. Volume 11:Issue 31(2020)
• Page Start: 8301
• Page End: 8305
• Publication Date: 2020-07-31
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02127j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A highly selective iron-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and sp 2 -hybridized Grignard reagents is reported. Abstract : A highly chemoselective iron-catalyzed three-component dicarbofunctionalization of unactivated olefins with alkyl halides (iodides and bromides) and sp 2 -hybridized Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp 2 -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.