Related Experiment Video
Updated: May 24, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Design and Development of Carbene-Catalyzed Intramolecular Vinylogous Stetter Reaction to Access Phenanthrol
Purna Chandra Behera1,2, Jakkula Ramarao1,2, Surisetti Suresh1,2
1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
Abstract:
The present study reveals the design and development of an N-heterocyclic carbene (NHC)-catalyzed intramolecular vinylogous Stetter reaction. This protocol enabled the synthesis of diverse phenanthrol derivatives and naphthol-fused heterocycles in very good to excellent yields. The success of the title reaction relies on the design of biaryl aldehydes bearing p-quinone methide (p-QM) moiety that acts as a vinylogous Stetter (1,6-conjugate) acceptor while the aldehyde functional group serves as an acyl anion equivalent, generated in situ from NHC-catalyzed umpolung. Salient features of the presented protocol include atom efficiency, operational simplicity, broad substrate scope, large-scale synthesis, and postsynthetic modifications.
More Related Videos
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
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...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

