Rhodium-Catalyzed [5 + 1 + 2] Reaction of Yne-Vinylcyclopropenes and CO: The Application of Vinylcyclopropenes for Higher-Order Cycloaddition DOI
Zhiqiang Huang, Zhi‐Xiang Yu

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

Transition metal-catalyzed higher-order cycloadditions involving vinylcyclopropenes (VCPEs) have not been realized to synthesize challenging medium-sized rings, partially due their poor stability and many competing side reactions. We report here a Rh-catalyzed [5 + 1 2] reaction of yne-VCPEs CO for the synthesis eight-membered carbocycles with trienone moiety, which so far can be accessed by only limited The key this cycloaddition is that once C-C cleavage VCPE (C5 synthon) form six-membered metallacycle initiated, (C1 insertion happens before alkyne (C2 insertion, attributing special reactivity sp2 carbon in vinylcyclopropene. Quantum chemical calculations applied support pathway. present has broad scope, C2 synthon also extended alkenes allene. Of same importance, catalyzed either [Rh(CO)2Cl]2 or cheaper complex, RhCl3·nH2O.

Language: Английский

DFT mechanistic study of Rh(I)-catalyzed C–C bond activation in benzocyclopentane alkoxy derivatives: Effects of substituents, ligands, and additives DOI

Jiangping Yang,

Guanghui Song,

Y. LI

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115097 - 115097

Published: April 10, 2025

Language: Английский

Citations

0
(Imido)tungsten-Alkylidene-Catalyzed [2+2+1]-Cycloaddition Reaction of 3,3-Disubstituted Cyclopropenes and Internal Alkynes Giving Multisubstituted Cyclopentadienes DOI

T. Akiyama,

Akira Yamamoto, Toshihiko Kasahara

et al.

Organometallics, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Language: Английский

Citations

0
Rhodium-Catalyzed [5 + 1 + 2] Reaction of Yne-Vinylcyclopropenes and CO: The Application of Vinylcyclopropenes for Higher-Order Cycloaddition DOI
Zhiqiang Huang, Zhi‐Xiang Yu

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

Transition metal-catalyzed higher-order cycloadditions involving vinylcyclopropenes (VCPEs) have not been realized to synthesize challenging medium-sized rings, partially due their poor stability and many competing side reactions. We report here a Rh-catalyzed [5 + 1 2] reaction of yne-VCPEs CO for the synthesis eight-membered carbocycles with trienone moiety, which so far can be accessed by only limited The key this cycloaddition is that once C-C cleavage VCPE (C5 synthon) form six-membered metallacycle initiated, (C1 insertion happens before alkyne (C2 insertion, attributing special reactivity sp2 carbon in vinylcyclopropene. Quantum chemical calculations applied support pathway. present has broad scope, C2 synthon also extended alkenes allene. Of same importance, catalyzed either [Rh(CO)2Cl]2 or cheaper complex, RhCl3·nH2O.

Language: Английский

Citations

0