Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Copper-Catalyzed Cross-Coupling of Allylboronic Acids with alpha-Diazoketones
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2015 (Engelska)Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, nr 19, s. 4754-4757Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Copper-catalyzed cross-coupling of substituted allylboronic acids with alpha-diazoketones was studied. This allylation reaction is highly regioselective, providing the branched allylic product. The process involves creation of a new C(sp(3))-C(sp(3)) bond by retaining the keto functional group of the alpha-diazoketone precursor.

Ort, förlag, år, upplaga, sidor
2015. Vol. 17, nr 19, s. 4754-4757
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-122944DOI: 10.1021/acs.orglett.5b02285ISI: 000362384700027OAI: oai:DiVA.org:su-122944DiVA, id: diva2:868750
Forskningsfinansiär
VetenskapsrådetKnut och Alice Wallenbergs StiftelseTillgänglig från: 2015-11-11 Skapad: 2015-11-11 Senast uppdaterad: 2018-06-21Bibliografiskt granskad
Ingår i avhandling
1. New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
Öppna denna publikation i ny flik eller fönster >>New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
2018 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. s. 61
Nyckelord
carbon-carbon bond formation, cross-coupling, organoboron compound, allylboron reagent, allylation, transition metal, metal carbene, allenylboron reagent, transition metal free, diazo compound, tosylhydrazone, quinone
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-157469 (URN)978-91-7797-340-9 (ISBN)978-91-7797-341-6 (ISBN)
Disputation
2018-09-07, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2018-08-15 Skapad: 2018-06-19 Senast uppdaterad: 2018-09-10Bibliografiskt granskad

Open Access i DiVA

Fulltext saknas i DiVA

Övriga länkar

Förlagets fulltext

Sök vidare i DiVA

Av författaren/redaktören
Wang, DongBelhomme, Marie-CharlotteSzabó, Kálmán J.
Av organisationen
Institutionen för organisk kemi
I samma tidskrift
Organic Letters
Organisk kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 83 träffar
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf