Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups

doi:10.1021/acs.joc.6b02772

	Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups
	Jiang, Quanbin 1; Yu, Zhengkun 1,2; Guo, Tenglong 1
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2017-02-17
卷号	82 期号:4 页码:1951-1960
ISSN号	0022-3263
DOI	10.1021/acs.joc.6b02772
文献子类	Article
英文摘要	Copper-catalyzed borylation of beta-trifluoromethyl-alpha,beta-unsaturated ketones was efficiently achieved by means of bis(pinacolato)diboron (B(2)pin(2)), affording the enantioenriched pfoducts in good yields with high enantioselectivities. CuI and (R,S)-Josiphos consist of the most efficient catalyst system under mild conditions. In the absence of the chiral ligand, the reactions could be performed more efficiently to form beta-ketone derivatives which were directly borylated and indirectly trifluoromethylated at the beta-carbon atom of the alpha,beta-unsaturated ketone substrates. The present protocol provides a promising method to access a stereogenic carbon center bearing both CF3 and organoboron functional groups.
WOS关键词	ELECTRON-DEFICIENT ALKENES ; BORON CONJUGATE ADDITIONS ; ENANTIOSELECTIVE SYNTHESIS ; BETA-BORATION ; ALPHA,BETA-UNSATURATED ACCEPTORS ; BETA,BETA-DISUBSTITUTED ENONES ; ALLYLIC ALCOHOLS ; QUINONE METHIDES ; BOND FORMATION ; ESTERS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000394736000011
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/169482]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Yu, Zhengkun
作者单位	1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
推荐引用方式 GB/T 7714	Jiang, Quanbin,Yu, Zhengkun,Guo, Tenglong. Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(4):1951-1960.
APA	Jiang, Quanbin,Yu, Zhengkun,&Guo, Tenglong.(2017).Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups.JOURNAL OF ORGANIC CHEMISTRY,82(4),1951-1960.
MLA	Jiang, Quanbin,et al."Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups".JOURNAL OF ORGANIC CHEMISTRY 82.4(2017):1951-1960.