Copper-free synthesis of skipped diynes via cross-coupling reactions of alkynylalanes with propargylic electrophiles

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5629-5632

  Kessabi, Jilali ^a   Beaudegnies, Renaud ^a   Jung, Pierre M J ^a   Martin, Benjamin ^a   Montel, Florian ^a   Wendeborn, Sebastian ^a  

^a SYNGENTA CROP PROTECTION AG   (Switzerland)

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[No Author keywords available]

Indexed keywords

EID: 33845969491     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0623769     Document Type: Article

References (49)

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44. See Supporting Information for experimental procedure.
45. The corresponding N,N-dimethyl carbamate behaved similarly according to GC analysis.
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49. The need for 2 equiv of alkynylalane when employing propargyl phosphates and phosphinates suggests that the reaction is proceeding via an alternative mechanism, essentially involving Lewis acid activation prior to coordination and transfer brought on by the second equivalent of alkynylalane.