Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 14, 2020
Previous Article Next Article

Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp3)–H bonds driven by visible light

Author affiliations

Abstract

Asymmetric cross-dehydrogenative coupling (CDC) of C(sp3)–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp3)–H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C–C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions.

Graphical abstract: Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp3)–H bonds driven by visible light

Back to tab navigation

Supplementary files

Article information


Submitted
21 Jan 2020
Accepted
18 Jun 2020
First published
19 Jun 2020

Green Chem., 2020,22, 4597-4603
Article type
Paper

Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp3)–H bonds driven by visible light

K. Zhou, Y. Yu, Y. Lin, Y. Li and L. Gong, Green Chem., 2020, 22, 4597
DOI: 10.1039/D0GC00262C

Social activity

Search articles by author

Spotlight

Advertisements