Arylboronic Acid Deborylation Deuteration via Synergistic Thiol, Lewis Base, and Photoredox Catalysis

Dong, Jianyang; Yu, Mo; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wu, Linan; Si, Duanyun; Cheng, Yang; Yang, Guang; Wang, Qingmin

doi:10.1021/acs.orglett.2c00722

Cited by 11 publications

(10 citation statements)

References 51 publications

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“…Arylboronic acids and esters have been widely used in organic synthesis due to the advantages they present of versatile transformations, low toxicity and air/moisture stability. In 2022, Wang and co-workers 38 disclosed the deborylation–deuteration under visible light irradiation. A broad range of arylboronic acids were successfully deuterated with a synergistic thiol, a Lewis base, and a photosensitizer catalytic system (Scheme 32).…”

Section: Radical Defunctionalization–deuterationmentioning

confidence: 99%

Radical deuteration

et al. 2022

Chem. Soc. Rev.

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Section: Radical Defunctionalization–deuterationmentioning

confidence: 99%

Radical deuteration

et al. 2022

Chem. Soc. Rev.

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“…The reaction was mediated by the synergistic combination of thiol, Lewis base, and photoredox catalysis. [140] As shown in Scheme 40, firstly, a Lewis base catalyst 131 combined with 4-benzyloxybenzeneboronic acid 129 to form complex 132. Meanwhile, the thiol catalyst 135 reacted with D 2 O to generate the deuterated thiol 136.…”

Section: Combining Lewis Base Catalysis With Photoredox Catalysismentioning

confidence: 99%

“…Based on the previous wok about aldehyde deuteration with D 2 O, [139] in 2022, Wang's group used arylboronic acids (readily available reagents) as radical precursors, developing a protocol for deborylation deuteration with D 2 O. The reaction was mediated by the synergistic combination of thiol, Lewis base, and photoredox catalysis [140] …”

Section: Combining Lewis Base Catalysis With Photoredox Catalysismentioning

confidence: 99%

Advanced Synthesis Using Photocatalysis Involved Dual Catalytic System

Guo

Wang

et al. 2022

Eur J Org Chem

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Combining visible‐light photoredox catalysis with other kinds of catalysis is a powerful strategy to address the barriers met in reactions driven by single catalyst. Under environmentally benign condition, photoredox catalysis produces radical species via visible light irradiation. These species then work with other catalysts, often resulting in unconventional reactivities, by which the scope of reaction could be expanded. Interest focusing on photocatalysis in the synthetic chemistry community has grown tremendously over the past five years, and one of the most striking emerging features is the development of dual catalytic approaches. This minireview summarizes the progress on this theme, mainly including dual catalytic systems merging photoredox activation with acid/base catalysts.

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“…Deuterium-labeled compounds have a wide range of applications in different research areas, such as analysis of drug metabolism, elucidating reaction mechanisms, and improving material properties . Notably, the synthesis of deuterium pharmaceutical agents has been increasingly used in new drug discovery in the past decade .…”

Section: Introductionmentioning

confidence: 99%

Visible-Light Photoredox-Catalyzed Decarboxylation of α-Oxo Carboxylic Acids to C1-Deuterated Aldehydes and Aldehydes

2022

J. Org. Chem.

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The synthesis of high-value-added C1-deuterated aldehydes would improve the availability of deuterated lead compounds for deuterium-labeled drug discovery. Herein, we develop a metal-free synthesis of C1-deuterated aldehydes with D2O from α-oxo carboxylic acids at ambient temperature. Via visible-light photoredox-catalyzed decarboxylation, stoichiometric reductants and oxidants were avoided. Various functional groups were tolerated and resulted in C1-deuterium aldehydes in up to 92% yield and 91–97% D incorporation under mild conditions. This method is also applied to the synthesis of various aldehydes. Primary mechanistic studies indicate that the catalytic pathway occurs via a reductive quenching pathway followed by hydrogen atom transfer.

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Arylboronic Acid Deborylation Deuteration via Synergistic Thiol, Lewis Base, and Photoredox Catalysis

Cited by 11 publications

References 51 publications

Radical deuteration

Radical deuteration

Advanced Synthesis Using Photocatalysis Involved Dual Catalytic System

Visible-Light Photoredox-Catalyzed Decarboxylation of α-Oxo Carboxylic Acids to C1-Deuterated Aldehydes and Aldehydes

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