Iron-Mediated Segment Coupling of Alkenols with Acceptors via C–C Radical Translocation and Remote Oxidative 1,5/6-Hydrogen Atom Transfer DOI
Santosh J. Gharpure, Rupali S. Chavan, Dipak J. Fartade

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9920 - 9925

Published: Nov. 8, 2024

Iron-mediated segment coupling followed by oxidative 1,5/6-hydrogen atom transfer (HAT) for synthesis of ε-oxo alkene derivatives is developed. This transformation involved translocation the radical from H-to-C-to-C-to-C oxidation under MHAT conditions providing rapid access to 1,6/1,7-keto functionalized esters/ketone/sulfones/phosphonates/arenes. The different outcomes with acceptors could be explained bond dissociation energies (BDEs), and mechanistic insights were gained through control experiments, including deuterium labeling studies.

Language: Английский

Fe(III)-Catalyzed Ring Expansion of Cyclopropenone from Olefins via Radicals to Access Pyrone and Indanone Derivatives DOI
Yao Xiao, Dongwei Huang,

Jie Liao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 11, 2025

A novel approach for the synthesis of pyrone and indanone derivatives utilizing Fe(III)-catalyzed reductive radical ring expansion olefins cyclopropenone has been proposed. The preliminary mechanism study shows that alkyl is formed by hydrogen atom transfer, which can open tension then generate intermediate. There are two paths intermediate: when there a hydroxyl group at β-position olefin, reaction produces pyrones, otherwise 1-indanone generated. This method mild conditions wide substrate adaptability allows fragment to be conveniently accessed.

Language: Английский

Citations

1
A Short Synthesis of the Long-Tailed Mealybug Pheromone in both Racemic and Enantiopure Forms DOI

Snehasish Senapati,

Ananth Kumar Ballari,

Chintalapudi Venkaiah

et al.

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

Published: March 24, 2025

The sex pheromone of the long-tailed mealybug has been synthesized in both racemic and enantiopure forms from simple acyloin acetate chiral acyloins (both R S). An efficient iron-mediated intramolecular radical cyclization used to achievethe formation a cyclopentane core bicyclic lactone bearing two quaternary centers under mild conditions. resulting lactones were elaborated give target pheromone.

Language: Английский

Citations

0
Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles DOI
Roger Machín Rivera,

Zack R. Ferrin,

Vincent N. G. Lindsay

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Language: Английский

Citations

3
Recent Advances of 5-Endo-trig Radical Cyclization: Promoting Strategies and Applications DOI
Yulu Zhou,

Sangxuan Xu,

Xuemei Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(74), P. 10098 - 10111

Published: Jan. 1, 2024

This review presents a concise summary of recent progress in the field 5- endo-trig radical cyclization, elucidating effective strategies for facilitating this significant yet challenging cyclization process.

Language: Английский

Citations

0
Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination DOI
Yongli Zhao,

Dingsheng Cao,

Jie‐Ping Wan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract The C3‐alkenylation of indoles have been developed by means a novel in situ iodination tactic which is capable mediating the Heck coupling with alkenes. method features specific site‐selectivity oriented C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well highly general tolerance to different terminal alkenes, including unactivated acrylates, acrylic acid, vinyl sulfone functionalized natural products.

Language: Английский

Citations

0
Iron-Mediated Segment Coupling of Alkenols with Acceptors via C–C Radical Translocation and Remote Oxidative 1,5/6-Hydrogen Atom Transfer DOI
Santosh J. Gharpure, Rupali S. Chavan, Dipak J. Fartade

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9920 - 9925

Published: Nov. 8, 2024

Iron-mediated segment coupling followed by oxidative 1,5/6-hydrogen atom transfer (HAT) for synthesis of ε-oxo alkene derivatives is developed. This transformation involved translocation the radical from H-to-C-to-C-to-C oxidation under MHAT conditions providing rapid access to 1,6/1,7-keto functionalized esters/ketone/sulfones/phosphonates/arenes. The different outcomes with acceptors could be explained bond dissociation energies (BDEs), and mechanistic insights were gained through control experiments, including deuterium labeling studies.

Language: Английский

Citations

0