Stereoselective Radical C–H Alkylation with Acceptor/acceptor-substituted Diazo Reagents Via Co(ii)-based Metalloradical Catalysis

Authors

Xin Cui, University of South Florida
Xue Xu, University of South Florida
Li-Mei Jin, University of South Florida
Lukasz Wojtas, University of South FloridaFollow
X. Peter Zhang, University of South Florida

Document Type

Article

Publication Date

2015

Digital Object Identifier (DOI)

https://doi.org/10.1039/C4SC02610A

Abstract

Co(II)-based metalloradical catalysis has, for the first time, been successfully applied for asymmetric intramolecular C–H alkylation of acceptor/acceptor-substituted diazo reagents. Through the design and synthesis of a new D2-symmetric chiral amidoporphyrin as the supporting ligand, the Co(II)-based metalloradical system, which operates at room temperature, is capable of 1,5-C–H alkylation of α-methoxycarbonyl-α-diazosulfones with a broad range of electronic properties, providing the 5-membered sulfolane derivatives in high yields with excellent diastereoselectivities and enantioselectivities. In addition to complete chemoselectivity toward allylic and allenic C–H bonds, the Co(II)-based metalloradical catalysis for asymmetric C–H alkylation features a remarkable degree of functional group tolerance.

Rights Information

This work is licensed under a Creative Commons Attribution 3.0 License.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Chemical Science, v. 6, issue 2, p. 1219-1224

Scholar Commons Citation

Cui, Xin; Xu, Xue; Jin, Li-Mei; Wojtas, Lukasz; and Zhang, X. Peter, "Stereoselective Radical C–H Alkylation with Acceptor/acceptor-substituted Diazo Reagents Via Co(ii)-based Metalloradical Catalysis" (2015). Chemistry Faculty Publications. 129.
https://digitalcommons.usf.edu/chm_facpub/129