[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles DOI Open Access

Binbin Wang,

Qiushan Gao,

Huanfeng Jiang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Language: Английский

Cu-catalyzed enantioselective assembly of axially chiral allylic boronates DOI
Shuai Wang, Jianbo Liu,

Wenyue Ma

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Language: Английский

Citations

4
Recent Developments in the [1,2]-Phospha-Brook Rearrangement Reaction DOI Open Access
Ning Li, Qian Wu,

Yu Huang

et al.

International Journal of Molecular Sciences, Journal Year: 2025, Volume and Issue: 26(7), P. 3065 - 3065

Published: March 27, 2025

The [1,2]-phospha-Brook rearrangement serves as a powerful synthetic strategy that enables efficient carbonyl umpolung through phosphoryl group migration, providing direct access to α-hydroxyphosphoryl compounds-a privileged class of synthons with broad applications in organophosphorus chemistry, medicinal and materials science. This review provides comprehensive overview recent progress methodologies, possible mechanisms, asymmetric transformations, highlighting key breakthroughs future directions this rapidly evolving field.

Language: Английский

Citations

0
Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols DOI
Ning Li, Qian Wu,

Yu Huang

et al.

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

Published: May 1, 2025

A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. library 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due its unique center-chiral scaffold.

Language: Английский

Citations

0
Access to Chiral Oxindoles via Ir-Catalyzed Asymmetric Pudovik Addition/[1,2]-Phospha-Brook Rearrangement/Allylation Cascade DOI
Bobin Chen,

Zhiyuan Yi,

Xiu‐Qin Dong

et al.

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

Published: May 2, 2025

An asymmetric catalytic Pudovik addition/[1,2]-phospha-Brook rearrangement/allylation reaction of readily available isatins, phosphites, and vinyl ethylene carbonate enabled by a chiral iridium catalyst was developed in one-pot fashion. A wide range enantioenriched oxindole derivatives containing two adjacent stereocenters could be obtained good to high yields with excellent diastereoselectivity enantioselectivity (65-99% yield, 7:1 >20:1 dr, generally 99% ee). This cascade protocol owned the advantages starting materials, regio-/diastereo-/enantioselectivity, substrate scope generality.

Language: Английский

Citations

0
[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles DOI Open Access

Binbin Wang,

Qiushan Gao,

Huanfeng Jiang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Language: Английский

Citations

2