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Copper-Catalyzed, Stereoselective Cross-Coupling of Cyclic Allyl Boronic Acids with alpha-Diazoketones
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 22017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 7, p. 1622-1625Article in journal (Refereed) Published
Abstract [en]

In this study; we present the synthesis of new, Stereodefined allylboronic adds employed to investigate the stereochemistry of the Cu-catalyzed cross-coupling of allylboronic acids with alpha-diazoketones. According to our results, this reaction proceeds with retention of the relative configurtion of the allylberonic acid substrate. We suggest that the stereoinduction step involves a syn S(E)2'-type transrnetalation of the allylboronic acid substrate with a Cu-carbene species.

Place, publisher, year, edition, pages
2017. Vol. 19, no 7, p. 1622-1625
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-143602DOI: 10.1021/acs.orglett.7b00433ISI: 000398985800033PubMedID: 28334535OAI: oai:DiVA.org:su-143602DiVA, id: diva2:1104023
Available from: 2017-05-31 Created: 2017-05-31 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

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