Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid

doi:10.1007/s11696-019-00962-z

	Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid
	Jiang, Wenfang 1; Shao, Guanghua 1; Liu, Ying 2; Du, Xin 1
刊名	CHEMICAL PAPERS
	2019-10-25
页码	7
关键词	Bromoallenes Unsymmetric 1,3-Diynes CuI/amino acid
ISSN号	2585-7290
DOI	10.1007/s11696-019-00962-z
英文摘要	Unsymmetric 1,3-diynes were synthesized by using bromoallenes as the starter substrates over the catalysts of CuI and amino acid. l-Proline was chosen as the amino acid as a suitable ligand of CuI. Inorganic bases, especially Cs2CO3, obviously facilitated the reaction. After screening the reaction solvents, such as CH2Cl2, DMF, Et2O, C6H5CH3, THF, CH3CN, DMSO and CH3C(O)CH3, DMSO was chosen as the best reaction solvent, and within the solvent, the yield of unsymmetric 1,3-diynes could achieve the good value of 72%. Under optimum conditions of CuI/l-proline, Cs2CO3 and DMSO, bromoallenes with methyl-, bromo- or chloro-groups in the para-position of aromatic rings gave more than 61% yields of unsymmetric 1,3-diynes. When bromoallenes had the ortho- or meta-bromine groups, the reaction failed and there were no products. The mechanism of formation of unsymmetric 1,3-diyne was also proposed as both processes of isomerization and subsequent elimination, which were catalyzed by the coupling of CuI with l-proline. Graphic abstract Scheme 1 Graphic abstract for the synthesis of unsymmetric 1,3-diynes [GRAPHICS] .
资助项目	National Natural Science Foundation of China[21576264] ; National Natural Science Foundation of China[21776285] ; National Natural Science Foundation of China[21571027]
WOS关键词	TERMINAL ALKYNES ; SELECTIVE SYNTHESIS ; CONJUGATED DIYNES ; COUPLING REACTION ; OXIDANT
WOS研究方向	Chemistry
语种	英语
出版者	SPRINGER INTERNATIONAL PUBLISHING AG
WOS记录号	WOS:000492341800001
资助机构	National Natural Science Foundation of China
内容类型	期刊论文
源URL	[http://ir.ipe.ac.cn/handle/122111/39070]
专题	中国科学院过程工程研究所
通讯作者	Liu, Ying; Du, Xin
作者单位	1.Dalian Univ Technol, Coll Chem, Dalian 116012, Peoples R China 2.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, State Key Lab Multiphase Complex Syst, Inst Proc Engn, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Jiang, Wenfang,Shao, Guanghua,Liu, Ying,et al. Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid[J]. CHEMICAL PAPERS,2019:7.
APA	Jiang, Wenfang,Shao, Guanghua,Liu, Ying,&Du, Xin.(2019).Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid.CHEMICAL PAPERS,7.
MLA	Jiang, Wenfang,et al."Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid".CHEMICAL PAPERS (2019):7.