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

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% cataly...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 14; pp. 3687 - 3690
Main Authors Li, Xiaoqing, Liao, Shengrong, Wang, Zhixun, Zhang, Liming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2017
Amer Chemical Soc
Subjects
Alkynes
Azides - chemical synthesis
Catalysis
Chemistry
Chemistry, Organic
Gold
Ligands
Molecular Structure
Physical Sciences
Science & Technology
C BOND-CLEAVAGE
NITROGENATION
ORGANIC AZIDES
VINYL AZIDES
HYDROAZIDATION
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Summary: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 °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.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01359