Synthesis of 1,1,1-Tris(boronates) from Vinylarenes by Co-Catalyzed Dehydrogenative Borylations–Hydroboration

The selective preparation of 1,1,1-tris­(boronates) from vinylarenes and bis­(pinacolato)­diboron is described. The reactions occur at ambient temperature with excellent selectivity, high yields, and good functional group tolerance. Mechanistic studies suggest that Co­(I)-catalyzed double dehydrogen...

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Published inJournal of the American Chemical Society Vol. 137; no. 50; pp. 15600 - 15603
Main Authors Zhang, Lei, Huang, Zheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.12.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALKENE ISOMERIZATION-HYDROBORATION
ASYMMETRIC-SYNTHESIS
CONSTRUCTION
COMPLEXES
SP-CARBON
DIBORYLATION
REACTIVITY
DIBORATION
H ACTIVATION
COBALT
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Summary:The selective preparation of 1,1,1-tris­(boronates) from vinylarenes and bis­(pinacolato)­diboron is described. The reactions occur at ambient temperature with excellent selectivity, high yields, and good functional group tolerance. Mechanistic studies suggest that Co­(I)-catalyzed double dehydrogenative borylations generate a 1,1-diborylalkene intermediate, which undergoes hydroboration with pinacolborane formed in situ to yield 1,1,1-tris­(boronate).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b11366