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Electrochemical C(sp 3 )-H Lactonization of 2-Alkylbenzoic Acids toward Phthalides.

Jee Eun HongJisong YoonWoohyun BaekKyumin KimJae-Hwan KwakYohan Park
Published in: Organic letters (2022)
Herein, we report direct electrochemical C(sp 3 )-H lactonization of 2-alkylbenzoic acids toward phthalides. The reaction provides a wide substrate scope of 2-alkylbenzoic acids bearing primary to tertiary C(sp 3 )-H bonds by utilizing a graphite anode, dichloromethane (DCM) solvent, hexafluoroisopropanol (HFIP) cosolvent, and n -Bu 4 NClO 4 electrolyte. Our synthetic approach offers a simple, intuitive, and atom-economical protocol to synthesize various phthalides (25 examples, up to 92% yield) and obtain other 5- and 6-membered lactones (10 examples, up to 83% yield).
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