Light-Driven Carbon–Carbon Coupling of α‑sp3–CH of Aliphatic Alcohols with sp2–CH Bond of 1,4-Naphthoquinones

Here, an α-selective Csp3–H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2 –Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C–H bonds (two sp3–C-H, one sp2–C...

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Bibliographic Details
Published in:Organic letters 2022-10, Vol.24 (41), p.7605-7610
Main Authors: Jha, Raushan Kumar, Upadhyay, Aditya, Kanika, Jain, Saket, K A, Neena, Kumar, Sangit
Format: Article
Language:English
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Summary:Here, an α-selective Csp3–H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2 –Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C–H bonds (two sp3–C-H, one sp2–C–H, and one O–H) and four new bonds formed, leading to fluorescent 2-acylated-1,4-naphthohydroquinones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03066