Work

Cascade MHAT Radical Cyclopentannulation of Skipped Enyne to Access Highly Functionalized Carbocycles

Year: 2026

Type: article

Abstract: An iron-mediated metal-hydride hydrogen atom transfer (MHAT) radical cyclization cascade has been developed for the efficient construction of highly functionalized carbocyclic frameworks. This versatile [3+2] cyclopentannulation strategy starting from skipped enynes provides rapid access to a broad range of alkylidene cyclopentanes/cyclopentenes. Termination of this cascade with various radical trapping agents allows efficient construction of annulated products via successive C-H/C-C/C-C/C-X bond (X = C, H, S, Se, Te, I) formation. The method allows an expeditious entry into diquinanes, angular triquinanes with 4 quaternary carbons (3 contiguous) and substituted cyclopentadienes, all amenable to complex carbocycle synthesis.

Source: JACS Au

DOI: 10.1021/jacsau.6c01108

Authors: Santosh J. Gharpure, Simran R. Narang, Rupali S. Chavan

Institution: Indian Institute of Technology Bombay

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Ministry of Education, India, Science and Engineering Research Board