Work

Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition–Polar Cyclization Cascade

Year: 2018

Type: article

Abstract: Herein, we describe the development of a photoredox-catalyzed decarboxylative radical addition-polar cyclization cascade approach to functionalized cyclopropanes. Reductive termination of radical-polar crossover reactions between aliphatic carboxylic acids and electron-deficient alkenes yielded carbanion intermediates that were intercepted in intramolecular alkylations with alkyl chlorides appended to the alkene substrate. The mild conditions, which make use of a readily available organic photocatalyst and visible light, were demonstrated to be amenable to a broad range of structurally complex carboxylic acids and a wide variety of chloroalkyl alkenes, demonstrating exquisite functional group tolerance.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201808598

Authors: Chao Shu, Riccardo S. Mega, Björn J. Andreassen, Adam Noble, Varinder K. Aggarwal

Institution: University of Bristol

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Horizon 2020 Framework Programme, Engineering and Physical Sciences Research Council, Biotechnology and Biological Sciences Research Council, H2020 European Research Council