uu.seUppsala University Publications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • 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
Control of Aryne Capture Regioselectivity via Fluoroboronate-induced Distortion
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Lukasz Pilarski)
2019 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

Arynes are valued as extremely versatile electrophilic intermediates. Control over the regioselectivity with which arynes react is typically achieved using comparatively simple and/or chemically inutile substituents close to the reactive triple bond. This poses a challenge for the broad acceptance of arynes as the basis of genuinely useful synthetic building blocks.

The work in this thesis attempts to overcome this limitation by developing a strategy in which the boronate ester functional group that drives the regioselectivity of an aryne capture is installed at a remote location of the molecule and offers ample opportunity for further derivatisation. This has been achieved via a catalytic C-H borylation strategy.

Using experimental, mechanistic and computational studies, we show that remote, boron-based functional group is temporarily activated in-situ into a form able to furnish unprecedented levels of aryne capture regioselectivity. After the aryne capture, the boronate may be used in myriad further manipulations to provide compounds that are difficult or impossible otherwise to synthesize.

Place, publisher, year, edition, pages
Acta Universitatis Upsaliensis, 2019. , p. 53
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-395449OAI: oai:DiVA.org:uu-395449DiVA, id: diva2:1362382
Presentation
2019-11-08, C8-317, 10:00 (English)
Opponent
Supervisors
Available from: 2019-10-22 Created: 2019-10-18 Last updated: 2019-10-22Bibliographically approved

Open Access in DiVA

No full text in DiVA

Authority records BETA

Hribersek, Matic

Search in DiVA

By author/editor
Hribersek, Matic
By organisation
Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric score

urn-nbn
Total: 12 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • 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