Copper-Catalyzed Dynamic Kinetic Asymmetric Arylation of Secondary Phosphine-Boranes for the Synthesis of P(III)-Stereogenic Centers
Transition-metal-catalyzed asymmetric C-P(III) bond formation is a direct method for the construction of P(III)-stereogenic centers; however, achieving high enantioselectivity remains a challenge. Herein, an unprecedented Cu-catalyzed dynamic kinetic resolution of secondary phosphine-boranes was successfully developed. This asymmetric C-P(BH<sub>3</sub>) coupling reaction provided the direct and highly enantioselective synthesis of P(III)-stereogenic centers, enabling the formation of chiral medium-sized benzophosphine-boranes (7-10-membered cycles). A mechanism of dynamic kinetic resolution involving the unusual rapid racemization of secondary phosphine-boranes has been proposed.
Authors
- Xiao Jin (ORCID: https://orcid.org/0000-0002-5423-0982)
- Deyin Wang (ORCID: https://orcid.org/0000-0002-3481-6679)
- Wenqiang Yang (ORCID: https://orcid.org/0000-0002-2918-1859)
- Zhen Wang (ORCID: https://orcid.org/0000-0003-4134-1779)
- Xue Wang (ORCID: https://orcid.org/0000-0001-8239-3693)
- Chun Zhang (ORCID: https://orcid.org/0000-0003-4422-173X)
- Lei Ge
- Xiaowei Shi
Institutions
- Linyi University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c00682
- Citations
- 2
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.07
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Government of Shandong Province