Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light‐Mediated Selective C‐C Cleavage Strategy DOI
Tin V. T. Nguyen, Duncan K. Brownsey, André Bossonnet

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

Abstract We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading selective cleavage more substituted carbon‐carbon bond. Depending substrate structure, extended alkenes were isolated or directly reacted in a photo‐Nazarov process bicyclic products. Based these results, unified reductive ring‐opening reaction was developed by using diphenyl disulfide as hydrogen atom transfer (HAT) reagent. By performing sequential cyclopropanation/selective ring opening reaction, we achieved CH 2 insertion into α,β bond both acyclic and cyclic unsaturated compounds. Our protocol provides further tool for modification carbon framework organic compounds, complementing recent progress “skeletal editing”.

Language: Английский

Brønsted-acid-mediated cyclocondensation towards dihydro-1-benzazepines DOI Creative Commons
Letian Xu, Alena M. Vasquez,

Jose M. Medina

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 162, P. 155572 - 155572

Published: April 10, 2025

Language: Английский

Citations

0
Seven-membered ring systems DOI

R. Alan Aitken

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 485 - 496

Published: Jan. 1, 2024

Citations

3
Silver- and Base-Enabled SOMOphilic Alkynylation of Alkylboronic Acids with Bromoalkynes DOI

Wenqian Du,

Rongjie Yang,

Jian-Shan Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

Alkynyl-containing molecules hold significant importance in organic synthesis, drug discovery, and materials science. Herein, we report an efficient protocol for the C(sp)-C(sp3) cross-coupling of bromoalkynes with primary, secondary, tertiary alkylboronic acids. Mechanistic experiments suggest that silver base enable generation alkyl radical intermediate from acid then undergo a cascade α-addition β-elimination alkynyl bromides, leading to construction bonds. This strategy features readily available starting materials, diverse substrates, mild easily handled reaction conditions.

Language: Английский

Citations

0
Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light‐Mediated Selective C‐C Cleavage Strategy DOI Creative Commons
Tin V. T. Nguyen, Duncan K. Brownsey, André Bossonnet

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading selective cleavage more substituted carbon-carbon bond. Depending substrate structure, extended alkenes were isolated or directly reacted in a photo-Nazarov process bicyclic products. Based these results, unified reductive ring-opening reaction was developed by using diphenyl disulfide as hydrogen atom transfer (HAT) reagent. By performing sequential cyclopropanation/selective ring opening reaction, we achieved CH

Language: Английский

Citations

1
Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light‐Mediated Selective C‐C Cleavage Strategy DOI
Tin V. T. Nguyen, Duncan K. Brownsey, André Bossonnet

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

Abstract We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading selective cleavage more substituted carbon‐carbon bond. Depending substrate structure, extended alkenes were isolated or directly reacted in a photo‐Nazarov process bicyclic products. Based these results, unified reductive ring‐opening reaction was developed by using diphenyl disulfide as hydrogen atom transfer (HAT) reagent. By performing sequential cyclopropanation/selective ring opening reaction, we achieved CH 2 insertion into α,β bond both acyclic and cyclic unsaturated compounds. Our protocol provides further tool for modification carbon framework organic compounds, complementing recent progress “skeletal editing”.

Language: Английский

Citations

0