Palladium catalyzed selective arylation of o-carboranes via B(4)–H activation: amide induced regioselectivity reversal DOI

Tao‐Tao Xu,

Ke Cao, Caiyan Zhang

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(96), P. 13603 - 13606

Published: Jan. 1, 2018

By changing the charge distribution of boron vertices via introducing an amide on cage B(9), selective B(4) arylation o-carboranes Suzuki-Miyaura coupling has been developed. A series o-carborane derivatives decorated with diverse active groups have synthesized moderate to good yields, which proved be further transformed a novel kind tri-substituted nido-carborane fused oxazole potential application in neutron capture therapy, organometallic as well coordination chemistry.

Language: Английский

Natural-Product-Directed Catalytic Stereoselective Synthesis of Functionalized Fused Borane Cluster–Oxazoles for the Discovery of Bactericidal Agents DOI

Rajesh Varkhedkar,

Fan Yang,

Rakesh Dontha

et al.

ACS Central Science, Journal Year: 2022, Volume and Issue: 8(3), P. 322 - 331

Published: Feb. 11, 2022

The identification of an alternative chemical space in order to address the global challenge posed by emerging antimicrobial resistance is very much needed for discovery novel lead compounds. Boron clusters are currently being explored drug due their unique steric and electronic properties. However, challenges associated with synthesis derivatization techniques these compounds have limited utility rapid construction a library molecules screening against various biological targets as molecular platform. Herein, we report transition-metal-catalyzed regioselective direct B-H alkylation-annulation closo-dodecaborate anion natural products such menthol camphor directing groups. This method allowed 1,2,3-trisubstituted clusters, which were evaluated terms antibacterial activity WHO priority pathogens. Several synthesized dodecaborate derivatives displayed medium- high-level bactericidal Gram-positive Gram-negative bacteria.

Language: Английский

Citations

34
Visible-Light-Promoted Nickel-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes via Boron-Centered Carboranyl Radicals DOI
Shimeng Li, Zuowei Xie

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(18), P. 7960 - 7965

Published: April 22, 2022

A general strategy for the generation of hypervalent boron-centered carboranyl radicals at B(3), B(4), and B(9) positions has been developed first time via visible-light-promoted iodine atom abstraction from iodo-o-carboranes by low-valent nickel complex. These react with various (hetero)arenes to afford a wide range cage B-arylated carborane derivatives room temperature in very good excellent yields broad substrate scope. Their electrophilicities are dependent on vertex charges follow order B(3) > B(4) B(9). Both visible light catalyst proved critical radicals. The involvement boron is supported control experiments. reaction mechanism associated these reactions also proposed. This offers new protocol selected vertex, leading facile synthesis large class substituted molecules.

Language: Английский

Citations

34
Electrochemical Cage Activation of Carboranes DOI Creative Commons
Long Yang, Zijing Zhang,

Becky Bongsuiru Jei

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(20)

Published: Feb. 11, 2022

Abstract Carboranes are boron–carbon molecular clusters that possess unique properties, such as their icosahedron geometry, high boron content, and delocalized three‐dimensional aromaticity. These features render carboranes valuable building blocks for applications in supramolecular design, nanomaterials, optoelectronics, organometallic coordination chemistry, neutron capture therapy (BNCT) agents. Despite tremendous progress this field, stoichiometric chemical redox reagents largely required the oxidative activation of carborane cages. In context, electrosyntheses represent an alternative strategy more sustainable syntheses. It is only recent few years considerable has been made electrochemical cage functionalization carboranes, which summarized Minireview. We anticipate electrocatalysis will serve increasingly powerful stimulus within current renaissance electrochemistry.

Language: Английский

Citations

33
Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes DOI
Yu Chen, Yik Ki Au, Yangjian Quan

et al.

Science China Chemistry, Journal Year: 2018, Volume and Issue: 62(1), P. 74 - 79

Published: Dec. 6, 2018

Language: Английский

Citations

58
Palladium catalyzed selective arylation of o-carboranes via B(4)–H activation: amide induced regioselectivity reversal DOI

Tao‐Tao Xu,

Ke Cao, Caiyan Zhang

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(96), P. 13603 - 13606

Published: Jan. 1, 2018

By changing the charge distribution of boron vertices via introducing an amide on cage B(9), selective B(4) arylation o-carboranes Suzuki-Miyaura coupling has been developed. A series o-carborane derivatives decorated with diverse active groups have synthesized moderate to good yields, which proved be further transformed a novel kind tri-substituted nido-carborane fused oxazole potential application in neutron capture therapy, organometallic as well coordination chemistry.

Language: Английский

Citations

54