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Modular synthesis of oligoacetylacetones via site-selective silylation of acetylacetone derivatives

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Title: Modular synthesis of oligoacetylacetones via site-selective silylation of acetylacetone derivatives
Authors: Sarkar, Parantap Browse this author
Inaba, Yuya Browse this author
Shirakura, Hayato Browse this author
Yoneda, Tomoki Browse this author →KAKEN DB
Inokuma, Yasuhide Browse this author →KAKEN DB
Issue Date: 7-May-2020
Publisher: Royal Society of Chemistry
Journal Title: Organic & biomolecular chemistry
Volume: 18
Issue: 17
Start Page: 3297
End Page: 3302
Publisher DOI: 10.1039/d0ob00501k
Abstract: Oligoacetylacetones consisting of 3,3-disubstituted pentane-2,4-diones were synthesized through a terminal silylation and oxidative coupling protocol. Highly selective formation of mono-enol silyl ethers of 3,3-disubstituted acetylacetones was achieved using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a base. Subsequent silver(i) oxide mediated coupling reactions provided tetraketones. Unique substituent dependence was found for the terminal-selective silylation of tetraketones. Finally, octaketones (tetramers of acetylacetone derivatives) with three types of monomer sequences were prepared in their discrete forms. Single crystal X-ray analysis revealed that the solid-state conformations of oligoketone chains were predominantly governed by the ketone sequence rather than substituents. However, differences in the packing structures induced by alkyl substituents led to significant differences in melting points for the structural isomers of octaketones.
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 猪熊 泰英

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