Trifluoromethyl Rhodium-Carbynoid in [2+1+2] Cycloadditions

doi:10.1002/anie.202318887

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	Trifluoromethyl Rhodium-Carbynoid in [2+1+2] Cycloadditions
	Zhao, Wen-Wen; Tian, Meng-Yang; Zhou, Yi-Lin; Liu, Lu-Jie; Tian, Shao-Fang; He, Chun-Yang; Yang, Xing-Zhi; Chen, Yong-Zheng; Han, Wen-Yong
	2024
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
卷号	63 期号:13 页码:-
摘要	Trifluoromethyl cationic carbyne (CF3C+:) possessing dual carbene-carbocation behavior emulated as trifluoromethyl metal-carbynoid (CF3C+=M) has not been explored yet, and its reaction characteristics are unknown. Herein, a novel alpha-diazotrifluoroethyl sulfonium salt was prepared and used in Rh-catalyzed three-component [2+1+2] cycloadditions for the first time with commercially available N-fused heteroarenes and nitriles, yielding a series of imidazo[1,5-a] N-heterocycles that are of interest in medicinal chemistry, in which the insertion of trifluoromethyl Rh-carbynoid (CF3C+=Rh) into C=N bonds of N-fused heteroarenes was involved. This strategy demonstrates synthetic applications in late-stage modification of pharmaceuticals, construction of CD3-containing N-heterocycles, gram-scale experiments, and synthesis of phosphodiesterase 10A inhibitor analog. These highly valuable and modifiable imidazo[1,5-a] N-heterocycles exhibit good antitumor activity in vitro, thus demonstrating their potential applications in medicinal chemistry.A novel alpha-diazotrifluoroethyl sulfonium salt was prepared, and it was applied in Rh-catalyzed three-component [2+1+2] cycloadditions for the first time, affording various imidazo[1,5-a] N-heterocycles under mild conditions. This strategy involved a unique trifluoromethyl Rh-carbynoid (CF3C+=Rh), wherein three new chemical bonds were forged at the alpha-carbon of trifluoromethyl in a single step.+ image
DOI	10.1002/anie.202318887
WOS记录号	WOS:001169645100001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/76260
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Zhao, Wen-Wen,Tian, Meng-Yang,Zhou, Yi-Lin,et al. Trifluoromethyl Rhodium-Carbynoid in [2+1+2] Cycloadditions[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024,63(13):-.
APA	Zhao, Wen-Wen.,Tian, Meng-Yang.,Zhou, Yi-Lin.,Liu, Lu-Jie.,Tian, Shao-Fang.,...&Han, Wen-Yong.(2024).Trifluoromethyl Rhodium-Carbynoid in [2+1+2] Cycloadditions.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,63(13),-.
MLA	Zhao, Wen-Wen,et al."Trifluoromethyl Rhodium-Carbynoid in [2+1+2] Cycloadditions".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63.13(2024):-.

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