Issue 2, 2015

Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(ii)-based metalloradical catalysis

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.

Graphical abstract: Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(ii)-based metalloradical catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Aug 2014
Accepted
12 Nov 2014
First published
12 Nov 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 1219-1224

Author version available

Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(II)-based metalloradical catalysis

X. Cui, X. Xu, L. Jin, L. Wojtas and X. P. Zhang, Chem. Sci., 2015, 6, 1219 DOI: 10.1039/C4SC02610A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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