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Copper‐Catalyzed Triboration of Terminal Alkynes Using B(2)pin(2): Efficient Synthesis of 1,1,2‐Triborylalkenes
We report herein the catalytic triboration of terminal alkynes with B(2)pin(2) (bis(pinacolato)diboron) using readily available Cu(OAc)(2) and P(n)Bu(3). Various 1,1,2‐triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP‐2) inhibitors, were...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972586/ https://www.ncbi.nlm.nih.gov/pubmed/31502712 http://dx.doi.org/10.1002/anie.201908466 |
Sumario: | We report herein the catalytic triboration of terminal alkynes with B(2)pin(2) (bis(pinacolato)diboron) using readily available Cu(OAc)(2) and P(n)Bu(3). Various 1,1,2‐triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP‐2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper‐catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2‐triborylalkenes in modest yields. The utility of these products was demonstrated by further transformations of the C−B bonds to prepare gem‐dihaloborylalkenes (F, Cl, Br), monohaloborylalkenes (Cl, Br), and trans‐diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare. |
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