Synthesis of Bench‐stable Polycyclic Organophosphorus Heterocycles via Staudinger‐type Annulations of ortho‐Azidophenols DOI
Zhenguo Wang, Wenjun Luo, Zhiwei Li

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(13)

Published: Dec. 23, 2023

The formation of a five- or six-membered ring is known to stabilize unstable molecular structures such as hemiacetals. This idea can also be extended other high-coordinated p-block element species. Herein, we synthesized two novel polycyclic organophosphorus heterocycles via Staudinger-type annulations. Reactions either ortho-phosphinoarenesulfonyl fluorides 1 ortho-phosphinobenzoic acid methyl esters 4 with ortho-azidophenols 2 gave rise penta-coordinated P(V) heterocycles, benzo-benzo-1,2,3-thiazaphospholo-1,3,2-oxazaphosphole (B-B-TAP-OAP) 3 and benzo-benzo-1,2-azaphospholo-1,3,2-oxazaphosphol-12-one (B-B-AP-OAP) 5 in satisfactory yields. It remarkable that are both bench-stable exhibit considerable stability 10 % aqueous tetrahydrofuran solution. Preliminary computational studies disclosed the nitrogen gas key driving force for In addition, strong Si-F bond another contributor annulation 2.

Language: Английский

P(V)-bis(amidophenolate) ligand cooperation: Stoichiometric C=O-bond cleavage in aldehydes and ketones DOI Creative Commons

Simon B. H. Karnbrock,

Christopher Golz, Manuel Alcarazo

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(53), P. 6745 - 6748

Published: Jan. 1, 2024

The cooperation between a geometrically constrained, highly electrophilic phosphorus(V) center, and an electronically rich tetradentate bis(amidophenolate) ligand enables the cleavage of CO bond from typical aldehydes ketones delivering iminio phosphoramidate species. amphiphilic nature these products, which is demonstrated through their reaction with Lewis acids bases, use as mild source silylium cations silanes, allowing selective reductive coupling to ethers under catalytic conditions.

Language: Английский

Citations

0
Highlights from the 57th Bürgenstock Conference on Stereochemistry 2024 DOI Creative Commons
Jesús Mosquera, Alessandro Bismuto

Chemical Science, Journal Year: 2024, Volume and Issue: 15(25), P. 9392 - 9396

Published: Jan. 1, 2024

Herein, we share an overview of the scientific highlights from speakers at latest edition longstanding Bürgenstock Conference.

Language: Английский

Citations

0
Structure-Constraint Induced Increase in Lewis Acidity of Tris(ortho-carboranyl)borane and Selective Complexation with Bestmann Ylides DOI Creative Commons

Libo Xiang,

Junyi Wang,

Alexander Matler

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The Lewis acidity of tris( o -carboranyl)borane has been further increased through a structural constraint caused by the linking two carborane units.

Language: Английский

Citations

0
Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties DOI
Chenchen Li, Haiyang Huang,

Longgen Sun

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 135(6)

Published: Dec. 16, 2022

Abstract Rigidly planar polycyclic phosphacycles featuring an internal dioxaphosphorane are promising photofunctional materials. However, the lack of efficient synthetic methods resulted in limited structural diversities which significantly hampered extensive study. Herein, we report a straightforward three‐component synthesis novel dioxaphosphorane‐fused diphosphacycles with distinctive photophysical properties. Control experiments and theory calculations were performed to account for plausible reaction mechanism. We also systematically investigated structure‐property relationships these unprecedented platforms by combining (X‐ray analysis, optical redox properties) theoretical computations. Based on their unique structure properties, fluorescent switch pH sensing was revealed dynamic ring‐opening/ring‐closing process.

Language: Английский

Citations

1
Synthesis of Bench‐stable Polycyclic Organophosphorus Heterocycles via Staudinger‐type Annulations of ortho‐Azidophenols DOI
Zhenguo Wang, Wenjun Luo, Zhiwei Li

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(13)

Published: Dec. 23, 2023

The formation of a five- or six-membered ring is known to stabilize unstable molecular structures such as hemiacetals. This idea can also be extended other high-coordinated p-block element species. Herein, we synthesized two novel polycyclic organophosphorus heterocycles via Staudinger-type annulations. Reactions either ortho-phosphinoarenesulfonyl fluorides 1 ortho-phosphinobenzoic acid methyl esters 4 with ortho-azidophenols 2 gave rise penta-coordinated P(V) heterocycles, benzo-benzo-1,2,3-thiazaphospholo-1,3,2-oxazaphosphole (B-B-TAP-OAP) 3 and benzo-benzo-1,2-azaphospholo-1,3,2-oxazaphosphol-12-one (B-B-AP-OAP) 5 in satisfactory yields. It remarkable that are both bench-stable exhibit considerable stability 10 % aqueous tetrahydrofuran solution. Preliminary computational studies disclosed the nitrogen gas key driving force for In addition, strong Si-F bond another contributor annulation 2.

Language: Английский

Citations

0