Cited by Copper-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles

The literature of heterocyclic chemistry, part XXII, 2022 DOI

Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

и другие.

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

Rh-Catalyzed Synthesis of Isobenzofurans via Donor/Donor-Type Metal Carbenoids and Their [4 + 2] Cycloaddition DOI

Naoki Morita,

S. Yoshikawa,

Eisuke Ota

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 20, 2025

A rhodium-catalyzed synthesis of isobenzofurans via donor- and donor-type metal carbenoids has been developed. Nosylhydrazones were used as carbene precursors, generating rhodium carbenoid species under basic conditions. These intermediates underwent intramolecular cyclization with ester groups to afford isobenzofurans, which subsequently participated in a highly endo-selective [4 + 2] cycloaddition maleimides other dienophiles. The reaction exhibited broad substrate scope, accommodating various aryl substituents while maintaining excellent regio- stereoselectivity. Mechanistic studies, including control experiments, NMR analysis, computational calculations, revealed that the proceeds through intermediate, leading formation isobenzofuran prior cycloaddition. endo-selectivity was found originate from difference activation energies between transition states, supported by studies. Additionally, isolation diazo intermediate its direct conversion confirmed stepwise nature transformation. This study expands utility organic synthesis, demonstrating their effectiveness constructing reactive mild

Язык: Английский

Процитировано

Group VIII metal difluorocarbene complexes: Synthesis and applications DOI