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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...

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Detalles Bibliográficos
Autores principales: Liu, Xiaocui, Ming, Wenbo, Friedrich, Alexandra, Kerner, Florian, Marder, Todd B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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
Descripción
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.