Substrate-controlled C-H or C-C alkynylation of cyclopropanes: generation of aryl radical cations by direct light activation of hypervalent iodine reagents

13Citations
Citations of this article
11Readers
Mendeley users who have this article in their library.

Abstract

We report the first oxidative C-H alkynylation of arylcyclopropanes. Irradiation of ethynylbenziodoxolone (EBX) reagents with visible light at 440 nm promoted the reaction. By the choice of the aryl group on the cyclopropane, it was possible to completely switch the outcome of the reaction from the alkynylation of the C-H bond to the oxyalkynylation of the C-C bond, which proceeded without the need for a catalyst, in contrast to previous works. The oxyalkynylation could also be extended to aminocyclopropanes as well as styrenes. Computations indicated that the C-H activation became a favoured nearly barrierless process in the presence of two ortho methyl groups on the benzene ring.

References Powered by Scopus

Advances in Synthetic Applications of Hypervalent Iodine Compounds

1544Citations
N/AReaders
Get full text

Acetylene Chemistry: Chemistry, Biology, and Material Science

800Citations
N/AReaders
Get full text

Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis

292Citations
N/AReaders
Get full text

Cited by Powered by Scopus

Recent progress in alkynylation with hypervalent iodine reagents

37Citations
N/AReaders
Get full text

Transformations based on direct excitation of hypervalent iodine(iii) reagents

10Citations
N/AReaders
Get full text

Azido-alkynylation of alkenes through radical-polar crossover

10Citations
N/AReaders
Get full text

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Nguyen, T. V. T., Wodrich, M. D., & Waser, J. (2022). Substrate-controlled C-H or C-C alkynylation of cyclopropanes: generation of aryl radical cations by direct light activation of hypervalent iodine reagents. Chemical Science, 8. https://doi.org/10.1039/d2sc04344k

Readers' Seniority

Tooltip

PhD / Post grad / Masters / Doc 5

71%

Professor / Associate Prof. 2

29%

Readers' Discipline

Tooltip

Chemistry 6

100%

Article Metrics

Tooltip
Social Media
Shares, Likes & Comments: 1

Save time finding and organizing research with Mendeley

Sign up for free