The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism

	The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism
	Liu, Chao-You ; Li, Yu ; Ding, Jin-Ying ; Dong,Dewen ; Han,Fushe
刊名	chemistry-a european journal
	2014
卷号	20 期号:8 页码:2373-2381
关键词	C-H 1 CLICK CHEMISTRY 2 DIARYLIODONIUM SALTS PHOTOCLICK CHEMISTRY ARYL COMPLEXES PALLADIUM ARYLATION 3-DIPOLAR CYCLOADDITION 5-DISUBSTITUTED TETRAZOLES
通讯作者	han,fs
英文摘要	the development of a highly efficient and practical protocol for the direct cn coupling of h-tetrazole and boronic acid was presented. a careful and patient optimization of a variety of reaction parameters revealed that this conventionally challenge reaction could indeed proceed efficiently in a very simple system, that is, just by stirring the tetrazoles and boronic acids under oxygen in the presence of different cu-i or cu-ii salts with only 5mol% loading in dmso at 100 degrees c. most significantly, the reaction could proceed very smoothly in a regiospecific manner to afford the 2,5-disubstituted tetrazoles in high to excellent yields. a mechanistic study revealed that both tetrazole and dmso are crucial for the generation of catalytically active copper species in the reaction process in addition to their role as reactant and solvent, respectively. it is demonstrated that in the reaction cycle, the cu-i catalyst could be oxidized to cu-ii by oxygen to form a [cut2d] complex (t=tetrazole anion; d=dmso) through an oxidative copper amination reaction. the cu-ii complex thus formed was confirmed to be the real catalytically active copper species. namely, the cu-ii complex disproportionates to aryl cu-iii and cu-i in the presence of boronic acid. facile elimination of the cu-iii species delivers the cn-coupled product. the results presented herein not only provide a reliable and efficient protocol for the synthesis of 2,5-disubstituted tetrazoles, but most importantly, the mechanistic results would have broad implications for the de novo design and development of new methods for cu-catalyzed coupling reactions.
收录类别	SCI
语种	英语
WOS记录号	WOS:000330903700032
内容类型	期刊论文
源URL	[http://ir.ciac.jl.cn/handle/322003/52400]
专题	长春应用化学研究所_长春应用化学研究所知识产出_期刊论文
推荐引用方式 GB/T 7714	Liu, Chao-You,Li, Yu,Ding, Jin-Ying,et al. The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism[J]. chemistry-a european journal,2014,20(8):2373-2381.
APA	Liu, Chao-You,Li, Yu,Ding, Jin-Ying,Dong,Dewen,&Han,Fushe.(2014).The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism.chemistry-a european journal,20(8),2373-2381.
MLA	Liu, Chao-You,et al."The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism".chemistry-a european journal 20.8(2014):2373-2381.