Ligand-Accelerated Gold-Catalyzed Addition of in Situ Generated Hydrazoic Acid to Alkynes under Neat Conditions

被引:45
作者
Li, Xiaoqing [1 ,2 ]
Liao, Shengrong [1 ]
Wang, Zhixun [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
[2] Zhejiang Univ Technol, Dept Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
关键词
C BOND-CLEAVAGE; VINYL AZIDES; ORGANIC AZIDES; NITROGENATION; HYDROAZIDATION;
D O I
10.1021/acs.orglett.7b01359
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct addition of in situ generated hydrazoic acid to alkynes is realized without solvent by using a gold catalyst derived from a recently designed remotely functionalized biaryl-2-ylphosphine ligand (i.e., WangPhos). With terminal alkynes, the additions are mostly realized with 0.1 mol% catalyst loadings and at 40 degrees C. With more challenging internal alkynes devoid of direct EWG substitution, the one-step transformation is realized for the first time, with generally high efficiency at ambient temperature.
引用
收藏
页码:3687 / 3690
页数:4
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