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Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

preprint
submitted on 24.09.2020 and posted on 25.09.2020 by Ziqing Zuo, Raphael Kim, Donald Watson

We report an asymmetric Ullmann-type homocoupling of ortho-(iodo)arylphosphine oxides and ortho-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.

Funding

NIH NIGMS (R01 GM102358)

History

Email Address of Submitting Author

dawatson@udel.edu

Institution

University of Delaware

Country

USA

ORCID For Submitting Author

0000-0003-4864-297X

Declaration of Conflict of Interest

no conflict of interest

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