Diboration of 3-substituted propargylic alcohols using a bimetallic catalyst system: access to ()-allyl, vinyldiboronates

The diboration of substituted propargylic alcohols has been achieved using a bimetallic Pd/Cu catalyst system. The in situ formation of a pentrafluoroboronic acid intermediate sufficiently activates the C-O bond towards dual catalysis affording ( Z )-allyl, vinyldiboronates stereoselectively. A Pd/C...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 71; pp. 1313 - 1316
Main Authors Peck, Cheryl L, Nekvinda, Jan, Santos, Webster L
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.09.2020
Royal Society of Chemistry
Subjects
Alcohols
Bimetals
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Substitutes
HYDROBORATION
CARBONATES
REAGENTS
ALLYLIC ALCOHOLS
FREE BORYLATION
1,1-DIBORYLALKENES
INTERNAL ALKYNES
METAL-FREE DIBORATION
ALLENES
EFFICIENT
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Summary:The diboration of substituted propargylic alcohols has been achieved using a bimetallic Pd/Cu catalyst system. The in situ formation of a pentrafluoroboronic acid intermediate sufficiently activates the C-O bond towards dual catalysis affording ( Z )-allyl, vinyldiboronates stereoselectively. A Pd/Cu catalyst system facilitates the diboration of unactivated propargylic alcohols with pentafluoroboronic acid and diboron to generate ( Z )-allyl, vinyldiboronates.
Bibliography:Electronic supplementary information (ESI) available: Experimental procedures and characterization of new compounds. See DOI
10.1039/d0cc03563g
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc03563g