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An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

preprint
submitted on 29.06.2020 and posted on 30.06.2020 by Chet Tyrol, Nang Yone, Connor Gallin, Jeffery Byers
By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Funding

American Chemical Society, Petroleum Research Fund (59542-ND1)

American Chemical Society, Green Chemistry Institute Pharmaceutical Roundtable (2016)

History

Email Address of Submitting Author

jeffery.byers@bc.edu

Institution

Boston College

Country

United States

ORCID For Submitting Author

0000-0002-8109-674X

Declaration of Conflict of Interest

No conflict of interest

Version Notes

This is version 1 of this manuscript.

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