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Issue 47, 2019
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Light-enabled metal-free pinacol coupling by hydrazine

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Abstract

Efficient carbon–carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C–C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.

Graphical abstract: Light-enabled metal-free pinacol coupling by hydrazine

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Supplementary files

Article information


Submitted
29 Jul 2019
Accepted
06 Oct 2019
First published
11 Oct 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10937-10943
Article type
Edge Article

Light-enabled metal-free pinacol coupling by hydrazine

Z. Qiu, H. D. M. Pham, J. Li, C. Li, D. J. Castillo-Pazos, R. Z. Khaliullin and C. Li, Chem. Sci., 2019, 10, 10937 DOI: 10.1039/C9SC03737C

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