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

Synthesis and reactivity of an N-heterocyclic carbene–stabilized diazoborane DOI
Chonghe Zhang, Christopher C. Cummins, Robert J. Gilliard

et al.

Science, Journal Year: 2024, Volume and Issue: 385(6706), P. 327 - 331

Published: July 18, 2024

Diazo compounds and organic azides are widely used as reagents for accessing valuable molecules in multiple areas of fundamental applied chemistry. Their capacity to undergo versatile chemical transformations arises from the reactive nature an incipient dinitrogen molecule at terminal position. In this work, we report synthesis characterization N-heterocyclic carbene (NHC)-stabilized diazoborane-a boron-centered analog diazoalkanes. The diazoborane displays a strong tendency release dinitrogen, thus serving borylene source, analogy diazoalkanes nitrene sources, respectively. Also reminiscent diazoalkane azide reactivity, serves 1,3-dipole that undergoes uncatalyzed [3+2] cycloaddition with unactivated alkyne, affording five-membered heterocycle after two-step rearrangement.

Language: Английский

Citations

6
Oxidation-Induced Nucleophilic Substitution at Electron-Rich B(12) Vertex in [CB11H12]– under Catalyst-Free Conditions DOI Creative Commons
Wenliang Sun, Yujie Jin, Yongtao Wang

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Highly regioselective B(12) substitutions of the monocarborane anion [CB11H12]- has been a challenge. Here, we synthesized stable B-O-N zwitterionic compound with an impressive yield (isolated up to 98%) and excellent regioselectivity at position under catalyst-free conditions. The kinetics, substituent effect, capture experiments are paired theoretical calculations, showing that reaction mechanism is oxidation-induced nucleophilic substitution. hydride abstracted by oxoammonium oxidant lower cleavage energy 4.2 kcal mol-1 than B(7-11) positions, thereby changing electronegativity upon conversion neutral [CB11H11], in turn giving very high for This work presents effective method synthesizing oxygen derivatives anion.

Language: Английский

Citations

0
A Pd-catalyzed route to carborane-fused boron heterocycles DOI Creative Commons

Mengjie Zhu,

Puzhao Wang,

WU Zheng-qiu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(27), P. 10392 - 10401

Published: Jan. 1, 2024

A Pd-catalyzed cross-coupling system has been developed to achieve vicinal diamination of 9,10-dibromo-carborane with NH-heterocycles and anilines. These products can be further converted carborane-fused six- seven-membered heterocycles.

Language: Английский

Citations

2
Antiaromatic 2-Azaboroles with π4σ2 Electronic Configuration DOI

Leibo Tan,

Jiaxin Chen, Xiaocui Liu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Similar to pyridine, which is a structural analog of benzene, 2-azaborole can be viewed as borole, in the CH group at 2-position replaced by an N atom. Due its unique π

Language: Английский

Citations

2
Transition-metal-like coordination chemistry of dicoordinate borylenes with organic azides DOI

Robert Witte,

Sourav Kar, Krzysztof Radacki

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8629 - 8632

Published: Jan. 1, 2024

A series of borylene-organoazide complexes have been synthesized from the reactions dicoordinate borylenes and organoazides.

Language: Английский

Citations

1
Reactivity study of Lewis superacidic carborane-based analogue of 9-bromo-9-borafluorene towards Lewis bases DOI

Libo Xiang,

Alexander Matler,

Leibo Tan

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(28), P. 11655 - 11658

Published: Jan. 1, 2024

The reactivity of the Lewis superacidic 3D analogue 9-bromo-9-borafluorene with various bases has been investigated.

Language: Английский

Citations

0
Formal (2+2) ring expansion prevails over (4+2) cycloaddition of a kinetically stabilized benzoborirene with reactive cycloaddends DOI Creative Commons
Marvin Sindlinger, Sonja M. Biebl, Markus Ströbele

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(73), P. 9986 - 9989

Published: Jan. 1, 2024

(2+2) prevails in cycloaddition reactions of benzoborirene with PTAD and 4,4′-bipyridyl-1,2,4,5-tetrazine.

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