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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 (engelsk)Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, nr 19, s. 4754-4757Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2015. Vol. 17, nr 19, s. 4754-4757
HSV kategori
Forskningsprogram
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
Swedish Research CouncilKnut and Alice Wallenberg FoundationTilgjengelig fra: 2015-11-11 Laget: 2015-11-11 Sist oppdatert: 2018-06-21bibliografisk kontrollert
Inngår i avhandling
1. New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
Åpne denne publikasjonen i ny fane eller vindu >>New Reactions with Allyl- and Allenylboron Reagents: Transition-Metal-Catalyzed and Transition-Metal-Free Carbon-Carbon Bond Formation Processes
2018 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. s. 61
Emneord
carbon-carbon bond formation, cross-coupling, organoboron compound, allylboron reagent, allylation, transition metal, metal carbene, allenylboron reagent, transition metal free, diazo compound, tosylhydrazone, quinone
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-157469 (URN)978-91-7797-340-9 (ISBN)978-91-7797-341-6 (ISBN)
Disputas
2018-09-07, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2018-08-15 Laget: 2018-06-19 Sist oppdatert: 2018-09-10bibliografisk kontrollert

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