Direct excitation of carbonyl cyclopropanes: From divergent photo-isomerization and annulation to unified reductive C-C cleavage DOI Creative Commons
Tin V. T. Nguyen, André Bossonnet, Duncan K. Brownsey

и другие.

Опубликована: Май 22, 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 HAT reagent. By performing sequential cyclopropanation/selective ring opening reaction, we achieved CH2 insertion into alpha,beta- bond both acyclic and cyclic unsaturated compounds. Our protocol therefore provides further tool for framework-editing carbocycles, complementing recent progress "skeletal editing" strategies.

Язык: Английский

Direct excitation of carbonyl cyclopropanes: From divergent photo-isomerization and annulation to unified reductive C-C cleavage DOI Creative Commons
Tin V. T. Nguyen, André Bossonnet, Duncan K. Brownsey

и другие.

Опубликована: Май 22, 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 HAT reagent. By performing sequential cyclopropanation/selective ring opening reaction, we achieved CH2 insertion into alpha,beta- bond both acyclic and cyclic unsaturated compounds. Our protocol therefore provides further tool for framework-editing carbocycles, complementing recent progress "skeletal editing" strategies.

Язык: Английский

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