Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)–H Lactonization of 2‑Alkylbenzoic Acids

A mild and practical C­(sp3)–H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mecha...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (15), p.5842-5847
Main Authors: Li, Sasa, Su, Mincong, Sun, Jie, Hu, Kunjun, Jin, Jian
Format: Article
Language:English
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Summary:A mild and practical C­(sp3)–H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01984