Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides
Xiao-Jie Liu1,2, Sheng-Yun Zhou1,2, Yuting Xiao1,2
1Key Laboratory of Jiangxi Province for Persistent Pollutant Control and Resource Recycling, Nanchang Hangkong University, Nanchang 330063, China.
Abstract:
A practical and eco-friendly strategy for the radical-mediated decarboxylative [3 + 2] and [4 + 2] annulation of enynals and γ,σ-unsaturated N-(acyloxy)phthalimides through the photoactivation of an electron donor-acceptor (EDA) complex has been developed. A wide range of primary, secondary, and tertiary alkyl N-hydroxyphthalimide (NHP) esters can be used as suitable substrates for the synthesis of fused ketones without any transition-metal catalysts or oxidants. This protocol features a broad substrate scope, excellent selectivity, and clean reaction conditions.
More Related Videos
Related Concept Videos
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...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
α-Alkylation of Ketones via Enolate Ions
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Cycloaddition Reactions: Overview


![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)