Iron-Catalyzed Enantioselective Multicomponent Cross-Couplings of -Boryl Radicals. Academic Article uri icon

abstract

  • Despite recent interest in the development of iron-catalyzed transformations, methods that use iron-based catalysts capable of controlling the enantioselectivity in carbon-carbon cross-couplings are underdeveloped. Herein, we report a practical and simple protocol that uses commercially available and expensive iron salts in combination with chiral bisphosphine ligands to enable the regio- and enantioselective (up to 91:9) multicomponent cross-coupling of vinyl boronates, (fluoro)alkyl halides, and Grignard reagents. Preliminary mechanistic studies are consistent with rapid formation of an -boryl radical followed by reversible radical addition to monoaryl bisphosphine-Fe(II) and subsequent enantioselective inner-sphere reductive elimination. From a broader perspective, this work provides a blueprint to develop asymmetric Fe-catalyzed multicomponent cross-couplings via the use of alkenes as linchpins to translocate alkyl radicals, modify their steric and electronic properties, and induce stereocontrol.

published proceedings

  • Org Lett

altmetric score

  • 2.1

author list (cited authors)

  • Youshaw, C. R., Yang, M., Gogoi, A. R., Rentera-Gmez, A., Liu, L., Morehead, L. M., & Gutierrez, O.

citation count

  • 1

complete list of authors

  • Youshaw, Cassandra R||Yang, Ming-Hsiu||Gogoi, Achyut Ranjan||Rentería-Gómez, Angel||Liu, Lei||Morehead, Lukas M||Gutierrez, Osvaldo

publication date

  • November 2023