Related Experiment Video
Updated: May 29, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Chemo-Selective Electrochemical Pinacol Coupling of Aldehydes and Ketones Using TMSN3 as a Promoter
Shengmei Guo1, Yunxiang Jiang2, Junpeng Yang1
1Department of Chemistry, Nanchang University, Nanchang 330031, P. R. China.
Abstract:
The pinacol coupling is a significant method for carbon-carbon bond formation. Here, we present an efficient electrochemical approach for pinacol coupling of aldehydes and ketones using TMSN3 as a sacrificial reagent. This method exhibits broad applicability to aryl, heteroaryl, and alkyl aldehydes/ketones with excellent chemo-selectivity and high yields (40 examples, up to 99% yield) under mild conditions. This method can also be applied in the selective reduction of phthalimides to hydroxyl lactams in good yields. The proposed mechanism was elucidated by control experiments and cyclic voltammetry.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
α-Alkylation of Ketones via Enolate Ions
Acid-Catalyzed Aldol Addition Reaction
Oxymercuration-Reduction of Alkenes