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Visible-light-induced organocatalyzed C(sp^(2))–H bond functionalization of 1,3-azoles with trifluoroacetylsilanes

Science China Chemistry 2024年第11期67卷 3662-3668页

作者： Zhengyu Li Zeguo Zhang Zhihan Zhang Gang Zhou Yizhi Zhang Shanshan Liu Xiao Shen The Institute for Advanced Studies Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationWuhan UniversityWuhan 430072China College of Chemistry Central China Normal UniversityWuhan 430079China

Previous carbene insertion to C–H bonds of 1,3-azoles relied on metal carbene species. Herein, we report a metal-free C(sp^(2))–H bond functionalization of 1,3-azoles with trifluoroacetylsilanes. The reaction features mild conditions, broad substrate scope and wide functional group tolerance. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trifluoroacetylsilanes under the photocatalyzed conditions: generating carbenes which undergo cyclopropanation and generating biradicals which promote ring-opening aromatization of the in situ generated fused cyclopropanes.

关键词： C(sp^(2))–H bond functionalization carbenes biradicals cyclopropanation brook rearrangement

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Synthesis of Organofluorine Compounds with Acylsilanes

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Chinese Journal of Chemistry 2024年第8期42卷 887-902页

作者： Youyuan Guo Gang Zhou Xiao Shen The Institute for Advanced Studies Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationWuhan University299 Bayi RoadWuhanHubei430072 China

Comprehensive Summary,Organofluorine compounds are central in synthetic chemistry,medicinal chemistry and material *** this review,we summarize the investigations on the synthesis of organofluorine compounds with *** the non-fluorinated acylsilanes,the in situ generation of difluoroenoxysilanes from the reactions of the acylsilanes with trifluoromethylation reagents is the major pathway,leading to the facile preparation of variousα,α-*** the fluoroalkylacylsilanes,apart from the in situ generation of difluoroenoxysilanes through anion brook rearrangement,radical brook rearrangement of the photoexcited acylsilanes and the selective control of reactivities of the biradicals pave the way for the synthesis of a variety of organofluorine *** general,most of these reactions gave racemic products,and the asymmetric synthesis of organofluorine compounds with acylsilanes is still rare,which would be a future.

关键词： Acylsilanes Organofluorine compounds brook rearrangement Radical rearrangement β-Fluoride elimination Asymmetric catalysis Photocatalysis Defluoroalkylation

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Unification of Anion Relay Chemistry(ARC) with the Takeda and Hiyama/Denmark Cross-Coupling Reactions:Identification of an Effective Silicon-Based Transfer Agent

Unification of Anion Relay Chemistry(ARC) with the Takeda an...

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化学使世界更美好——中国化学会第七届有机化学学术会议

作者： Amos B.Smith Ⅲ Department of Chemistry Penn Center for Molecular Discovery and the Monell Chemical Senses CenterUniversity of PennsylvaniaPhiladelphiaPA19123

Anion Relay Chemistry(ARC),an effective multi-component union protocol,recently developed and employed in our laboratory,holds great potential for chemists requiring rapid increase of molecular complexity in a single operation,with precise control of stereogenicity on route to both natural and "natural product-like" targets for biomedical research. Employing this technique,a large number of diverse structures can be assembled rapidly from a small number of initiating nucleophiles,bifunctional linchpins,and electrophiles in a controlled,multi-component coupling *** to expand the scope of this tactic include the construction of natural products, as well as libraries of "natural product-like" compounds, which highlight the robust nature of this *** of the ARC tactic,involving both TypeⅠand TypeⅡprotocols,will be presented with illustrations arising from alkaloid and polyketide/macrolide total synthetic ventures currently ongoing in our *** addition,observations regarding the intersection of the ARC TypeⅡprotocol with previously reported reaction pathways, notably in the area of Pd-mediated Takeda and Hiyama/Denmark cross-coupling reactions,will be presented.

关键词： Anion Relay Chemistry Natural Product Synthesis Diversity-Oriented Synthesis brook rearrangement Cross-Coupling

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