Construction of C-C bonds via photoreductive coupling of ketones and aldehydes in the metal-organic-framework MFM-300(Cr)

Tian Luo, Lili Li, Yinlin Chen, Jie An (), Chengcheng Liu, Zheng Yan, Joseph H. Carter, Xue Han, Alena M. Sheveleva, Floriana Tuna, Eric J. L. McInnes, Chiu C. Tang, Martin Schröder () and Sihai Yang ()
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Tian Luo: University of Manchester
Lili Li: University of Manchester
Yinlin Chen: University of Manchester
Jie An: China Agricultural University
Chengcheng Liu: University of Manchester
Zheng Yan: University of Manchester
Joseph H. Carter: University of Manchester
Xue Han: University of Manchester
Alena M. Sheveleva: University of Manchester
Floriana Tuna: University of Manchester
Eric J. L. McInnes: University of Manchester
Chiu C. Tang: Harwell Science Campus
Martin Schröder: University of Manchester
Sihai Yang: University of Manchester

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Construction of C-C bonds via reductive coupling of aldehydes and ketones is hindered by the highly negative reduction potential of these carbonyl substrates, particularly ketones, and this renders the formation of ketyl radicals extremely endergonic. Here, we report the efficient activation of carbonyl compounds by the formation of specific host-guest interactions in a hydroxyl-decorated porous photocatalyst. MFM-300(Cr) exhibits a band gap of 1.75 eV and shows excellent catalytic activity and stability towards the photoreductive coupling of 30 different aldehydes and ketones to the corresponding 1,2-diols at room temperature. Synchrotron X-ray diffraction and electron paramagnetic resonance spectroscopy confirm the generation of ketyl radicals via confinement within MFM-300(Cr). This protocol removes simultaneously the need for a precious metal-based photocatalyst or for amine-based sacrificial agents for the photochemical synthesis.

Date: 2021
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DOI: 10.1038/s41467-021-23302-w

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