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Photocatalytic direct borylation of carboxylic acids

Qiang Wei, Yuhsuan Lee, Weiqiu Liang, Xiaolei Chen, Bo-shuai Mu, Xi-Yang Cui, Wangsuo Wu, Shuming Bai and Zhibo Liu ()
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Qiang Wei: Peking University
Yuhsuan Lee: Chinese Academy of Sciences
Weiqiu Liang: Peking University
Xiaolei Chen: Lanzhou University
Bo-shuai Mu: Peking University
Xi-Yang Cui: Peking University
Wangsuo Wu: Lanzhou University
Shuming Bai: Chinese Academy of Sciences
Zhibo Liu: Peking University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.

Date: 2022
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DOI: 10.1038/s41467-022-34833-1

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