Microwave-assisted or Cu-NHC-catalyzed cycloaddition of azido-disubstituted alkynes: Bifurcation of reaction pathways

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9818-9825

  Xia, Yuyu ^a   Chen, Ling Yan ^a   Lv, Shang ^a   Sun, Zhihua ^a   Wang, Bing ^b  

^a SHANGHAI UNIVERSITY OF ENGINEERING SCIENCE   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROCARBONS; STEREOCHEMISTRY;

CHEMICAL EQUATIONS; INTERMOLECULAR CYCLOADDITION; MICROWAVE-ASSISTED; PROPARGYLIC AMINES; REACTION PATHWAYS; SIDE-CHAINS;

MICROWAVE IRRADIATION;

ACETAMIDE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; AZIDE; COPPER; SILANE DERIVATIVE; TRIAZOLE DERIVATIVE; ALKYNE; PARGYLINE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; MICROWAVE RADIATION; SYNTHESIS;

ALKYNES; AMINES; AZIDES; CATALYSIS; COPPER; CYCLOADDITION REACTION; MICROWAVES; MOLECULAR STRUCTURE; PARGYLINE; TRIAZOLES;

EID: 84908191311     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5011262     Document Type: Article

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58. Slow addition of a dilute solution of the same substrate to the Cu-NHC catalyst produced the "dimer" and "trimer" in a 65:35 ratio (as determined by LC-MS). We thank one of the reviewers for the constructive suggestion of the possibility of reaction kinetics involving a quasi-stationary low concentration of the desilyled alkyne intermediate.