Issue 10, 2022

Metal-free oxidative formal C(sp2)–H arylation of cyclopentene-1,3-diones with β-naphthols

Abstract

An efficient, mild, and transition-metal free formal C(sp2)–H arylation of prochiral 2,2-disubstituted cyclopentene-1,3-diones is reported. This oxidative arylation with β-naphthols proceeds via base-mediated C-Michael addition followed by aerial oxygen insertion and a subsequent α-hydroperoxy elimination sequence. This operationally simple and environmentally benign transformation is highly scalable and does not require any pre-functionalization. Moreover, this reaction affords excellent yields of α-substituted β-naphthols bearing all-carbon quaternary centers.

Graphical abstract: Metal-free oxidative formal C(sp2)–H arylation of cyclopentene-1,3-diones with β-naphthols

Supplementary files

Article information

Article type
Communication
Submitted
25 Jan 2022
Accepted
14 Feb 2022
First published
15 Feb 2022

Org. Biomol. Chem., 2022,20, 2059-2063

Metal-free oxidative formal C(sp2)–H arylation of cyclopentene-1,3-diones with β-naphthols

S. Maurya, S. B. Jadhav and R. Chegondi, Org. Biomol. Chem., 2022, 20, 2059 DOI: 10.1039/D2OB00156J

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