Visible-Light-Mediated Rose Bengal- or [Ru(bpy)3]2+-Catalyzed Radical [4 + 2] Cycloaddition: An Efficient Route to Tetrahydrocarbazoles DOI Creative Commons

Cody Bishir,

Abigail Hubbard,

Liangyong Mei

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(10), P. 10713 - 10723

Published: March 7, 2025

A visible-light-induced Rose Bengal- or [Ru(bpy)3]2+-catalyzed radical [4 + 2] cycloaddition of redox-active indole N-hydroxyphthalimide esters with electron-deficient alkenes has been developed. This base-free protocol provides a facile and powerful route for the synthesis functionalized biologically significant tetrahydrocarbazoles under mild conditions. On one hand, when an organic photocatalyst-Rose Bengal was employed green light, desired were obtained in up to 82% yield. other reaction yield increased 93% presence [Ru(bpy)3Cl2]·6H2O blue light. The success gram-scale transformation experiments, as well photopromoted [5 further highlight practicality robustness this protocol. Mechanistic studies also support generation crucial alkyl intermediate.

Language: Английский

Visible-Light-Mediated Rose Bengal- or [Ru(bpy)3]2+-Catalyzed Radical [4 + 2] Cycloaddition: An Efficient Route to Tetrahydrocarbazoles DOI Creative Commons

Cody Bishir,

Abigail Hubbard,

Liangyong Mei

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(10), P. 10713 - 10723

Published: March 7, 2025

A visible-light-induced Rose Bengal- or [Ru(bpy)3]2+-catalyzed radical [4 + 2] cycloaddition of redox-active indole N-hydroxyphthalimide esters with electron-deficient alkenes has been developed. This base-free protocol provides a facile and powerful route for the synthesis functionalized biologically significant tetrahydrocarbazoles under mild conditions. On one hand, when an organic photocatalyst-Rose Bengal was employed green light, desired were obtained in up to 82% yield. other reaction yield increased 93% presence [Ru(bpy)3Cl2]·6H2O blue light. The success gram-scale transformation experiments, as well photopromoted [5 further highlight practicality robustness this protocol. Mechanistic studies also support generation crucial alkyl intermediate.

Language: Английский

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