Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Tunable cross coupling of silanols: Selective synthesis of heavily substituted allenes and butadienes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2012 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 134, no 38, 15992-15999 p.Article in journal (Refereed) Published
Abstract [en]

1,3-Dienyl-2-silanols with a wide range of substitution patterns are readily obtained by palladium-catalyzed silaboration of 1,3-enynes followed by Suzuki-Miyaura cross coupling with aryl bromides. Subsequent Hiyama-Denmark cross coupling with aryl iodides provides either 1,3- or 1,2-dienes in high yields. The site selectivity can be fully controlled by the choice of activator used in the coupling reaction. In the presence of strong bases such as NaOt-Bu, KOt-Bu, and NaH, clean formation of 1,2-dienes takes place via allylic rearrangement. In contrast, stereo- and site-selective formation of tetra- and trisubstituted 1,3-dienes results from use of Ag 2O and Bu 4NF·3H 2O, respectively, as activators. Under microwave heating at 100 °C the base-mediated cross couplings are largely accelerated and are completed within one hour or less. The ratio of diastereomeric allenes varies depending on the substitution pattern of the silanol and ranges from >99:1 to 52:48.

Place, publisher, year, edition, pages
2012. Vol. 134, no 38, 15992-15999 p.
Keyword [en]
1, 2-dienes, 1, 3-dienes, Allenes, Allylic rearrangement, Aryl bromides, Aryl iodides, Coupling reaction, Cross-couplings, Diastereomeric, High yield, Palladium-catalyzed, Selective synthesis, Silaboration, Silanols, Site selective, Site selectivity, Substitution patterns, Suzuki-Miyaura, Butadiene, Silver oxides, Olefins, 1, 3 butadiene, alkene derivative, allene derivative, iodine derivative, silanol, article, controlled study, cross coupling reaction, diastereoisomer, quantum yield, Suzuki reaction, synthesis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-105327DOI: 10.1021/ja3070717ISI: 000309099700058Scopus ID: 2-s2.0-84866721008OAI: oai:DiVA.org:kth-105327DiVA: diva2:570715
Funder
Swedish Research Council
Note

QC 20121120

Available from: 2012-11-20 Created: 2012-11-20 Last updated: 2017-05-30Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Authority records BETA

Moberg, Christina

Search in DiVA

By author/editor
Zhou, HuiMoberg, Christina
By organisation
Organic Chemistry
In the same journal
Journal of the American Chemical Society
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 56 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf