Formation of N-sulfonylamidines by copper-catalyzed coupling of sulfonyl azides, terminal alkynes, and trialkylamines

Tetrahedron Letters

Volumn 52, Issue 6, 2011, Pages 668-670

  Yavari, Issa ^a   Ahmadian, Salome ^a   Ghazanfarpur Darjani, Majid ^a   Solgi, Yazdan ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Copper catalyst; N Sulfonylamidine; Sulfonyl azide; Terminal alkyne; Trialkylamine

Indexed keywords

ALIPHATIC AMINE; ALKYNE; AMIDINE; AZIDE; COPPER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLOADDITION; ONE POT SYNTHESIS;

EID: 79251596810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.135     Document Type: Article

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15. 2), 31.8 (MeN), 47.2 (CHN), 48.7 (CHN), 126.1 (2CH), 129.0 (2CH), 141.3 (C), 143.5 (C), 172.0 (CN).
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17. 3/2,6- lutidine at 0 °C to prevent intermediate 6 from decomposing and provide selective formation of the desired 1-sulfonyltriazoles.
18. Although a 1,3-dipole or a carbene (without migration of the Cu) would fit the data, we prefer the mechanism shown in Scheme 2.