Palladium Catalyzed Selective B(3)–H Activation/Oxidative Dehydrogenative Coupling for the Synthesis of Bis(o-carborane)s DOI

Ji Wu,

Ke Cao, Caiyan Zhang

et al.

Inorganic Chemistry, Journal Year: 2020, Volume and Issue: 59(23), P. 17340 - 17346

Published: Nov. 24, 2020

A palladium catalyzed selective B(3)-H activation/oxidative dehydrogenative coupling for the synthesis of bis(o-carborane)s connected with B(3)-B(3') and B(3)-B(6') bonds has been developed first time. plausible mechanism involving stepwise activation B(3'/6')-H by PdII PdIV was proposed. This work is example most efficient protocol bonds, which important reference design, synthesis, application in related fields.

Language: Английский

Nonclassical Applications of closo-Carborane Anions: From Main Group Chemistry and Catalysis to Energy Storage DOI
Steven P. Fisher, Anton W. Tomich,

Sergio Lovera

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(14), P. 8262 - 8290

Published: Feb. 1, 2019

Classically closo-carborane anions, particularly [HCB11H11]- and [HCB9H9]-, their derivatives have primarily been used as weakly coordinating anions to isolate reactive intermediates, platforms for stoichiometric catalytic functionalization, counteranions simple Lewis acid catalysis, components of materials like liquid crystals. The aim this article is educate the reader on contemporary nonclassical applications these anions. Specifically, review will cover new directions in main group catalysis utilized achieve some most challenging reactions such C-F, C-H, C-C functionalizations that are difficult or impossible realize with transition metals. In addition, utilization clusters dianionic C σ-bound ligands coordination chemistry, ligand substituents chemistry advanced catalyst design, covalently bound spectator stabilize radicals. Furthermore, solution-based solid-state electrolytes Li, Na, Mg batteries be discussed.

Language: Английский

Citations

258

Metal-catalyzed cross-coupling chemistry with polyhedral boranes DOI
Rafal M. Dziedzic, Alexander M. Spokoyny

Chemical Communications, Journal Year: 2018, Volume and Issue: 55(4), P. 430 - 442

Published: Nov. 28, 2018

Over the past several decades, metal-catalyzed cross-coupling has emerged as a powerful strategy to functionalize polyhedral borane clusters.

Language: Английский

Citations

119

Palladium-Catalyzed Selective Five-Fold Cascade Arylation of the 12-Vertex Monocarborane Anion by B–H Activation DOI
Furong Lin,

Jing-Lu Yu,

Yunjun Shen

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(42), P. 13798 - 13807

Published: Sept. 19, 2018

A series of cage penta-arylated carboranes have been synthesized by palladium-catalyzed intermolecular coupling the C-carboxylic acid monocarba- closo-dodecaborate anion [CB11H12]- with iodoarenes direct B-H bond functionalization. These transformations set a record in terms one-pot directing group-mediated activation inert bonds single molecule. The methodology is characterized high yields, good functional group tolerance, and complete regioselectivity. COOH can be easily removed during or after reaction. mechanistic pathways were probed using density theory calculations. Pd(II)-Pd(IV)-Pd(II) catalytic cycle proposed, which initial followed preferred adjacent boron vertex, continuation this selectivity results continuous walking process palladium center. opens new avenue toward building blocks 5-fold symmetry.

Language: Английский

Citations

95

Teaching an old dog new tricks: new directions in fundamental and applied closo-carborane anion chemistry DOI
Steven P. Fisher, Anton W. Tomich, Juchen Guo

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(12), P. 1684 - 1701

Published: Jan. 1, 2019

In this feature article we cover new directions in the fundamental and applied chemistry of closo-carborane anions [HCB11H11]−1 [HCB9H9]−1, including energy storage applications, ionic liquids, anionic carborane fused heterocycles/radicals, ligand substituents, ligands for catalysis coordination chemistry.

Language: Английский

Citations

81

Boron cluster anions and their derivatives in complexation reactions DOI
Varvara V. Avdeeva, Еlena А. Malinina, Nikolay T. Kuznetsov

et al.

Coordination Chemistry Reviews, Journal Year: 2022, Volume and Issue: 469, P. 214636 - 214636

Published: June 16, 2022

Language: Английский

Citations

63

A Carboranyl Electrolyte Enabling Highly Reversible Sodium Metal Anodes via a “Fluorine‐Free” SEI DOI Creative Commons
Anton W. Tomich, Jehee Park, Seoung‐Bum Son

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(51)

Published: Oct. 27, 2022

Realization of practical sodium metal batteries (SMBs) is hindered due to lack compatible electrolyte components, dendrite propagation, and poor understanding anodic interphasial chemistries. Chemically robust liquid electrolytes that facilitate both favorable deposition a stable solid-electrolyte interphase (SEI) are ideal enable anode-free cells. Herein we present advanced characterization novel fluorine-free utilizing the [HCB11 H11 ]1- anion. Symmetrical Na cells operated with this exhibit remarkably low overpotential 0.032 V at current density 2.0 mA cm-2 high coulombic efficiency 99.5 % in half-cell configurations. Surface electrodes post-operation reveals absence dendritic nucleation surprisingly SEI. Furthermore, weak ion-pairing identified as key towards successful development electrolytes.

Language: Английский

Citations

49

Chemistry of three-dimensional icosahedral boron clusters anions: closo-dodecaborate (2-) [B12H12]2- and carba-closo-dodecaborate(-) [CB11H12]- DOI
Lingyao Wang,

Yunjia Jiang,

Simon Duttwyler

et al.

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 516, P. 215974 - 215974

Published: June 8, 2024

Language: Английский

Citations

15

Thecloso‐Dodecaborate Dianion Fused with Oxazoles Provides 3D Diboraheterocycles with Selective Antimicrobial Activity DOI

Yuji Sun,

Jianglin Zhang, Yuanbin Zhang

et al.

Chemistry - A European Journal, Journal Year: 2018, Volume and Issue: 24(41), P. 10364 - 10371

Published: May 8, 2018

Abstract The synthesis and application of icosahedral boron cluster compounds has been studied extensively since their discovery several decades ago; however, two aspects chemistry have received little attention: possibility to form inorganic/organic fused boraheterocycles potential act as antimicrobial agents. This work comprises the preparation a class 3D diborabenzoxazole analogues with closo ‐dodecaborate in place benzene moiety. presented synthetic procedures provide access wide range diboraheterocycles under mild conditions. These heterocycles exhibit strong selective activity against Neisseria gonorrhoeae , widespread bacterial pathogen that shown increasing incidences multidrug resistance for which development new is urgently needed.

Language: Английский

Citations

64

Rhodium-Catalyzed Amidation of the Cage B(4)–H Bond in o-Carboranes with Dioxazolones by Carboxylic Acid-Assisted B(4)–H Bond Activation DOI
Yonghyeon Baek, Suhui Kim, Jeong‐Yu Son

et al.

ACS Catalysis, Journal Year: 2019, Volume and Issue: 9(11), P. 10418 - 10425

Published: Sept. 27, 2019

A rhodium-catalyzed direct and regioselective amidation of the cage B(4)–H bond in a wide range o-carboranes with alkyl-, aryl-, heteroaryl-substituted dioxazolones is demonstrated by carboxylic acid-assisted activation carborane clusters, providing number amidated high yields release carbon dioxide. Moreover, selective 2-fold decarboxylative reaction o-carborane was accessed.

Language: Английский

Citations

62

Old Key Opens the Lock in Carborane: The in Situ NHC-Palladium Catalytic System for Selective Arylation of B(3,6)–H Bonds of o-Carboranes via B–H Activation DOI

Tao‐Tao Xu,

Ke Cao, Caiyan Zhang

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(22), P. 9276 - 9279

Published: Nov. 5, 2019

An efficient in situ Pd-NHC catalytic system for regioselective arylation of B(3,6)-H bonds o-carborane has been developed the first time. A series symmetric and unsymmetric 3,6-diaryl-o-carboranes anchored with active groups have synthesized moderate to good yields under mild conditions. This work offers an protocol selective activation important value design coupling reactions functionalization o-carboranes.

Language: Английский

Citations

58