CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

Hua Wang; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.orglett.1c00537

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

Hua Wang, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

University of Science and Technology of China

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

Original language	English
Pages (from-to)	2900-2903
Number of pages	4
Journal	Organic Letters
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.1c00537
State	Published - 16 Apr 2021

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title = "CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling",

abstract = "A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.",

author = "Hua Wang and Qu, {Jian Ping} and Kang, {Yan Biao}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c00537",

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T1 - CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

AU - Wang, Hua

AU - Qu, Jian Ping

AU - Kang, Yan Biao

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N2 - A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

AB - A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

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JO - Organic Letters

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CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

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