Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides by NaI/PPh3 Catalysis

Xiao-Jie Liu; Sheng-Yun Zhou; Yuting Xiao; Qing Sun; Xin Lu; Yang Li; Jin-Heng Li

doi:10.1021/acs.orglett.1c02858

Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides by NaI/PPh₃ Catalysis

Org Lett. 2021 Oct 15;23(20):7839-7844. doi: 10.1021/acs.orglett.1c02858. Epub 2021 Sep 28.

Authors

Xiao-Jie Liu^{1

2}, Sheng-Yun Zhou^{1

2}, Yuting Xiao^{1

2}, Qing Sun^{1

2}, Xin Lu^{1

2}, Yang Li^{1

2}, Jin-Heng Li^{1

2}

Affiliations

¹ Key Laboratory of Jiangxi Province for Persistent Pollutant Control and Resource Recycling, Nanchang Hangkong University, Nanchang 330063, China.
² State Key Laboratory of Physical Chemistry of Solid Surface and Fujian Provincial Key Laboratory for Theoretical and Computational Chemistry, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

PMID: 34581593
DOI: 10.1021/acs.orglett.1c02858

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.