| Autor: |
Youshaw, Cassandra R., Yang, Ming-Hsiu, Gogoi, Achyut Ranjan, Rentería-Gómez, Angel, Liu, Lei, Morehead, Lukas M., Gutierrez, Osvaldo |
| Zdroj: |
Organic Letters; November 2023, Vol. 25 Issue: 46 p8320-8325, 6p |
| Abstrakt: |
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 α-boryl radical followed by reversibleradical 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. |
| Databáze: |
Supplemental Index |
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