Synthesis of Carboranylated Dihydropyrrolo[1,2-a]quinoxalines and Dihydroindolo[1,2-a]quinoxalines by BF3·OEt2-Catalyzed Heterocyclization of C-Formyl-o-carboranes and Investigation of Their Oxidation Stability DOI

Zhen-Zhen Sun,

Pan Gao, Yong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3573 - 3579

Published: Feb. 20, 2024

A BF3·OEt2-catalyzed synthesis of carboranylated dihydropyrrolo[1,2-a]quinoxalines and dihydroindolo[1,2-a]quinoxalines in 30–99% yields is presented through the heterocyclization various C-modified C-formyl-o-carboranes with 1-(2-aminophenyl)-pyrroles/indoles. systematic comparative investigation their oxidation stability air confirmed that 4-carboranyl-4,5-dihydropyrrolo[1,2-a]quinoxaline had better than 4-phenyl analogue. cage-deboronation reaction for N-acetyl-substituted dihydropyrrolo[1,2-a]quinoxaline produced corresponding 7,8-nido-carborane cesium salt. kinetic resolution was also realized to obtain an optically pure N-heterocycle scaffold bearing a carborane cage carbon-bonded chiral stereocenter.

Language: Английский

Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes DOI
Yaqi Liu, Rui Yang, Hongfang Li

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for highly regioselective functionalization pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis also applicable late-stage pharmaceutically complex molecules.

Language: Английский

Citations

0
Breaking the Base Barrier: Cu(II)-Mediated C–H Heteroarylation of o-Carboranes with Base-Sensitive Heteroaryl Halides DOI

Mengfan Sun,

Leijun Feng,

Ju‐You Lu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3697 - 3702

Published: April 30, 2024

While cage C-arylation reactions using strong bases are among the most frequently used transformations in carborane chemistry, there has been no general solution to allow for use of weak reaction. Moreover, base-metal-promoted C-H heteroarylation with base-sensitive heteroaryl halides remained elusive. Herein, copper-mediated (hetero)arylation achieved without need bases, leading facile synthesis a wide range C-(hetero)arylated carboranes good excellent yields broad substrate scope and functional group compatibility.

Language: Английский

Citations

2
Five-membered ring systems: Pyrroles and benzo analogs DOI
Chuan Shan, Justin M. Lopchuk

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

Citations

0
Synthesis of Carboranylated Dihydropyrrolo[1,2-a]quinoxalines and Dihydroindolo[1,2-a]quinoxalines by BF3·OEt2-Catalyzed Heterocyclization of C-Formyl-o-carboranes and Investigation of Their Oxidation Stability DOI

Zhen-Zhen Sun,

Pan Gao, Yong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3573 - 3579

Published: Feb. 20, 2024

A BF3·OEt2-catalyzed synthesis of carboranylated dihydropyrrolo[1,2-a]quinoxalines and dihydroindolo[1,2-a]quinoxalines in 30–99% yields is presented through the heterocyclization various C-modified C-formyl-o-carboranes with 1-(2-aminophenyl)-pyrroles/indoles. systematic comparative investigation their oxidation stability air confirmed that 4-carboranyl-4,5-dihydropyrrolo[1,2-a]quinoxaline had better than 4-phenyl analogue. cage-deboronation reaction for N-acetyl-substituted dihydropyrrolo[1,2-a]quinoxaline produced corresponding 7,8-nido-carborane cesium salt. kinetic resolution was also realized to obtain an optically pure N-heterocycle scaffold bearing a carborane cage carbon-bonded chiral stereocenter.

Language: Английский

Citations

0