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Updated: Jan 11, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Acid-promoted dehydroxylation coupling of aryl alcohols with 1,3-dicarbonyls and sulfonamides
Jiaxin Liang1, Chengxiu Liu1, Yuqiu Liang1
1Jiangxi Province Key Laboratory of Pharmacology of Traditional Chinese Medicine, School of Pharmacy, Gannan Medical University, Ganzhou, 341000, Jiangxi Province, People's Republic of China.
Abstract:
The formation of C-C and C-N bonds is an effective means to construct functional complex molecules. Herein, the TsOH-promoted dehydroxylation coupling of diarylmethanols with 1,3-dicarbonyls and sulfonamides to afford a variety of N-alkylated1,3-dicarbonyls and sulfonamides was established with only H2O as the byproduct. Differential 1,3-dicarbonyls and sulfonamides, including pharmaceutical molecules (sulfinpyrazone, phenylbutazone, mofebutazone, celecoxib, topiramate, valdecoxib) were compatible with this system to couple with alcohols in moderate to excellent yields. This method shows the merits of wide substrate scope and mild conditions.
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