Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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
Direct Allylation of Quinones with Allylboronates
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2015 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 6, p. 3343-3348Article in journal (Refereed) Published
Abstract [en]

Allylboronates undergo C-H allylation of unsubstituted or monosubstituted benzoquinone and naphthoquinone substrates. In the case of 2,5- or 2,6-disubstituted quinones addition involving the substituted carbon takes place. Allylation with stereodefined allylboronates occurs with retention of the configuration.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2015. Vol. 80, no 6, p. 3343-3348
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-116999DOI: 10.1021/acs.joc.5b00264ISI: 000351558400045PubMedID: 25728494OAI: oai:DiVA.org:su-116999DiVA, id: diva2:811892
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note

AuthorCount:3;

Available from: 2015-05-13 Created: 2015-05-05 Last updated: 2018-06-21Bibliographically approved
In thesis
1. New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
Open this publication in new window or tab >>New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Organoboron compounds have been widely used in carbon-carbon bond formation reactions in organic synthesis and catalysis. This thesis is focused on cross-coupling reactions of allyl-, allenylboronic acids and their ester derivatives via transition metal catalysis or transition-metal-free processes.

The first part of the thesis describes Cu-catalyzed C(sp3)-C(sp3) formation reactions involving allylboronic acids and α-diazoketones. This coupling process shows high γ-regioselectivity, resulting in branched allylic products. When stereodefined cyclic allylboronic acids were employed as the substrate, the relative facial configuration was retained in the reaction product.

The second part involves Pd-catalyzed cross-coupling of allylboronic acid and α-diazoketones. The reaction proceeds with high α-regioselectivity, affording linear allylic products. Accordingly, the palladium- and copper-catalyzed cross-coupling of allylboronic acid and α-diazoketones occurs with opposite regioselectivity.

The third part concerns a new transition-metal-free carbon-carbon bond formation between allenylboronic acids and in situ generated diazo compounds. The diazo compounds are generated from tosylhydrazones in the presence of base. The reaction is suitable for synthesis of densely substituted conjugated dienes with high Z-selectivity.

In the final part, the allylation of quinones with allylboronates is presented. The reaction was performed without any catalyst or additive. Various quinones can be employed as substrates, including unsubstituted, monosubstituted benzoquinones and naphthoquinones.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. p. 61
Keywords
carbon-carbon bond formation, cross-coupling, organoboron compound, allylboron reagent, allylation, transition metal, metal carbene, allenylboron reagent, transition metal free, diazo compound, tosylhydrazone, quinone
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-157469 (URN)978-91-7797-340-9 (ISBN)978-91-7797-341-6 (ISBN)
Public defence
2018-09-07, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Available from: 2018-08-15 Created: 2018-06-19 Last updated: 2018-09-10Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textPubMed

Search in DiVA

By author/editor
Deng, Hong-PingWang, DongSzabó, Kálmán J.
By organisation
Department of Organic Chemistry
In the same journal
Journal of Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
pubmed
urn-nbn

Altmetric score

doi
pubmed
urn-nbn
Total: 66 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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