Highly chemoselective nickel-catalyzed three-component cross-trimerization between two distinct terminal alkynes and an internal alkyne

Organic Letters

Volumn 13, Issue 1, 2011, Pages 122-125

  Ogata, Kenichi ^a   Atsuumi, Yuka ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

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EID: 78650859618     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102687p     Document Type: Article

References (29)

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6. For examples of cross-dimerization of alkynes involving bulky silylacetylene, see
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24. Structure of 4 was confirmed by NOESY.
25. 4). In this case, homodimer of 1 was confirmed as the main product by GC-MS.
26. In this case, [2 + 2 + 2] cycloaddition reaction of phenylacetylene was confirmed by GC-MS.
27. Another regioisomer of 4hg was confirmed by GC.
28. 2/phosphine by reaction with a terminal alkyne is usually postulated, See ref 2 and reference therein.
29. In the reaction with trimethylsilylacetylene instead of triisopropylsilylacetylene, the selective three-component reaction did not proceed, and a 2:1 cross-trimerization product involving two molecules of trimethylsilylacetylenes and a diphenylacetylene was formed in 21% isolated yield. This two-component cross-trimerization product has been reported, ref 4b.