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DIPEA-induced activation of OH^- for the synthesis of amides via photocatalysis.

ABSTRACT: The development of green protocols for photocatalysis where water acts as a nucleophile, induced by a weak organic base, is difficult to achieve in organic chemistry. Herein, an efficient light-mediated strategy for the synthesis of amides in which a weak organic base acts as a reductant to induce the formation of OH- from water under metal-free conditions is reported. A mechanistic study reveals that the generation of an N,N-diisopropylethylamine (DIPEA) radical via single electron transfer (SET), with the assistance of photocatalyst, that increases the nucleophilicity of the water molecules with respect to the cyanides is essential. Moreover, the removal rate of nitrile in wastewater can be as high as 83%, indicating that this strategy has excellent potential for nitrile degradation.

SUBMITTER: Wu M

PROVIDER: S-EPMC9109258 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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DIPEA-induced activation of OH- for the synthesis of amides via photocatalysis.

Wu Mei M Huang Sheng S Hou Huiqing H Lin Jie J Lin Mei M Zhou Sunying S Zheng Zhiqiang Z Sun Weiming W Ke Fang F

RSC advances 20220516 23

The development of green protocols for photocatalysis where water acts as a nucleophile, induced by a weak organic base, is difficult to achieve in organic chemistry. Herein, an efficient light-mediated strategy for the synthesis of amides in which a weak organic base acts as a reductant to induce the formation of OH- from water under metal-free conditions is reported. A mechanistic study reveals that the generation of an N,N-diisopropylethylamine (DIPEA) radical via single ...[more]

PMID: 35702194

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