Nanogold-Catalyzed cis-Silaboration of Alkynes with Abnormal Regioselectivity

The first example of gold-catalyzed silaboration of alkynes with PhMe2SiBpin is documented in the presence of supported gold nanoparticles. In the case of terminal alkynes, the reaction proceeds at ambient conditions in very good yields and the regio­selectivity is opposite to that observed in the p...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 5; pp. 1430 - 1433
Main Authors Gryparis, Charis, Stratakis, Manolis
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.03.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GOLD NANOPARTICLES
ORGANIC-SYNTHESIS
PALLADIUM
ACTIVATION
TRANSITION-METAL-COMPLEXES
TERMINAL ALKYNES
COPPER
STEREOSELECTIVE-SYNTHESIS
SI BONDS
PLATINUM COMPLEXES
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Summary:The first example of gold-catalyzed silaboration of alkynes with PhMe2SiBpin is documented in the presence of supported gold nanoparticles. In the case of terminal alkynes, the reaction proceeds at ambient conditions in very good yields and the regio­selectivity is opposite to that observed in the presence of Pd or Pt catalysts. The abnormal regio­selectivity is attributed to steric factors imposed by the Au nanoparticle during the 1,2-addition of silyl­borane to the alkyne.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500225x