Related Experiment Video
Updated: Sep 16, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
A Catalytic Approach to Intramolecular Wittig Reaction: Sulfonyl-Masked EDO Precursors Enabling Access to
Pei-Shan Wu1, Bo-Xuan Pan1, Po-Chung Chien1
1Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan, R.O.C.
Abstract:
We report an efficient catalytic protocol for the intramolecular Wittig reaction enabled by the PIII/PV redox cycle, starting from Ts-containing electron-deficient olefin (EDO) precursors, leading to EDOs that are traditionally inaccessible. This reaction proceeds through a cascade sequence involving the in situ generated EDO from EDO precursor/phospha-Michael addition/O-acylation/intramolecular Wittig reaction. This strategy exhibits broad substrate scope, high chemoselectivity, and excellent functional group tolerance. The mechanistic investigations revealed that the EDO precursor undergoes an in situ Ts-elimination and addition process during the reaction.
More Related Videos
Related Concept Videos
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Preparation and Reactions of Sulfides
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

