Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes DOI
Shimeng Li, Jie Zhang, Zuowei Xie

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7497 - 7501

Published: Oct. 6, 2022

This work describes a general method for the efficient production of class cage B-centered carboranyl radicals at B3, B4, and B9 sites via visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as starting materials. The electrophilicities these hypervalent boron-centered decrease in following order: B3 > B4 B9. They are useful intermediates preparation family B-(hetero)arylated o-carboranes ambient temperature.

Language: Английский

Charge Transfer Complex-Enabled Synthesis of (Hetero)arylated m-Carboranes from m-Carborane Phosphonium Salts DOI

Qing-Shuang Zhang,

Lin He, Qiang Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(31), P. 5768 - 5773

Published: Aug. 3, 2023

A photoinduced charge transfer complex (CTC)-enabled photoreduction of carborane phosphonium salts for the cage carbon (hetero)arylation carboranes was developed. It offers a convenient approach introducing wide range aryl and heteroaryl groups, such as pyrroles, thiophenes, indoles, thianaphthenes, benzofurans, pyridines, benzenes, into carboranes. This strategy operational simplicity, mild reaction conditions, broad substrate scope, making it highly advantageous.

Language: Английский

Citations

4

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

1

Metal-Catalyzed and Metal-Free Nucleophilic Substitution of 7-I-B18H21 DOI
Kierstyn P. Anderson, Peter I. Djurovich, Victoria P. Rubio

et al.

Inorganic Chemistry, Journal Year: 2022, Volume and Issue: 61(38), P. 15051 - 15057

Published: Sept. 13, 2022

In this work, two pathways of reactivity are investigated to generate site-specific substitutions at the B7 vertex luminescent boron cluster, anti-B18H22. First, a palladium-catalyzed cross-coupling reaction utilizing precursor 7-I-B18H21 and series model nucleophiles was developed, ultimately producing several B-N- B-O-substituted species. Interestingly, B-I bond in cluster can also be substituted an uncatalyzed fashion, leading formation various B-N, B-O, B-S products. This work highlights intricate differences corresponding these analyzes role solvents additives on product distributions. As result our synthetic studies, seven new B18-based clusters were synthesized, isolated, characterized by mass spectrometry nuclear magnetic resonance (NMR) spectroscopy. The photoluminescence properties structurally similar ether thioether products further investigated, with both exhibiting blue fluorescence solution 298 K long-lived green or yellow phosphorescence 77 K. Overall, shows, for first time, ability perform substitution boron-halogen resulting photoluminescent molecules.

Language: Английский

Citations

7

Ruthenium‐Catalyzed Selective B(4)‐H Amidation of o‐Carboranes with Dioxazolones DOI
Heejin Yang, Hee Chan Noh, Phil Ho Lee

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 12(3)

Published: Dec. 21, 2022

Abstract A ruthenium‐catalyzed selective B4 amidation of o ‐carboranes with a variety alkyl‐, aryl‐, and heteroaryl‐substituted dioxazolones is developed by carboxylic acid‐assisted B(4)‐H bond activation in ‐carborane acids, affording multitude (4)‐amidated good yields the evolution carbon dioxide. In addition, two‐fold decarboxylative reaction cage was accomplished.

Language: Английский

Citations

7

Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes DOI
Shimeng Li, Jie Zhang, Zuowei Xie

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7497 - 7501

Published: Oct. 6, 2022

This work describes a general method for the efficient production of class cage B-centered carboranyl radicals at B3, B4, and B9 sites via visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as starting materials. The electrophilicities these hypervalent boron-centered decrease in following order: B3 > B4 B9. They are useful intermediates preparation family B-(hetero)arylated o-carboranes ambient temperature.

Language: Английский

Citations

6