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Photocatalyzed borylation using water-soluble quantum dots

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Abstract

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Graphical abstract: Photocatalyzed borylation using water-soluble quantum dots

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Publication details

The article was received on 02 Mar 2019, accepted on 23 Apr 2019 and first published on 23 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC01737B
Chem. Commun., 2019, Advance Article

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    Photocatalyzed borylation using water-soluble quantum dots

    H. B. Chandrashekar, A. Maji, G. Halder, S. Banerjee, S. Bhattacharyya and D. Maiti, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC01737B

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