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Synthesis of Organofluorine Compounds with acylsilanes

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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Carbon-oxygen bond formation via visible-light-induced O-H insertion between acylsilanes and oximes

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Green Synthesis and Catalysis 2022年第2期3卷 194-197页

作者： Bao Gui Cai Qian Li Lei Li Jun Xuan Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province College of Chemistry&Chemical EngineeringAnhui UniversityHefei 230601China Key Laboratory of Structure and Functional Regulation of Hybrid Materials(Anhui University) Ministry of EducationHefei 230601China

Visible light promoted C-O bond formation reaction through O-H insertion of acylsilanes with oximes has been *** reaction occurred under mild reaction conditions(sole blue LED irradiation in the absence of any catalys... 详细信息

关键词： Visible light acylsilanes Siloxy carbene Oximes C-O bond formation

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Versatile Synthesis ofα-Oxygen Organoboron Compounds via Photo-Induced Siloxycarbene

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Chinese Journal of Chemistry 2024年第22期42卷 2712-2716页

作者： Xiongxiong Lu Qingbin Zhao Dehai Cao Pan Xu Xuenian Chen Zhenxing Liu College of Chemistry Zhengzhou UniversityZhengzhouHenan 450001China Henan Key Laboratory of Boron Chemistry and Advanced Materials Schoolof Chemistry and Chemical EngineeringHenan Normal UniversityXinxiangHenan 453007China

Comprehensive Summary A novel method for synthesizingα-oxygen organoboron compounds has been developed through acylsilane-based carbene insertion reactions into C—B *** coupling partners,readily available organoboron compounds(alkenyl,allyl,and allenyl B(pin))were *** on the substrates,pure insertion into C—B bonds or insertion followed by a siloxy group rearrangement process(from carbon to boron)would occur,delivering theα-oxygen organoboron compounds with great *** experiments demonstrated that the electronic effect of the substituents mainly controlled the rearrangement ***,no matter which isomer of substrate(Z or E)was used,the reaction withβ-aryl-substituted alkenyl B(pin)affords both isomers of products(Z and E,separable through column chromatography).Trapping experiments indicated the triplet energy transfer process was involved.

关键词： acylsilanes Siloxy carbenes Organoboron compounds Isomerization Photocatalysis Rearrangement

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Organocatalyzed direct aldol reaction of silyl glyoxylates for the synthesis of α-hydroxysilanes

Organocatalyzed direct aldol reaction of silyl glyoxylates f...

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Man-Yi Han Xiaoyu Xie Di Zhou Pinhua Li Lei Wang Department of Chemistry Huaibei Normal University Anhui

Due to their structural uniqueness, α-hydroxysilanes have attracted considerable attentions both for their preparation and synthetic utilities, and the development of efficient method for their preparation is highly demanding. In particular, the direct enantioselective installation of silicon into molecules is becoming increasingly significant.1 To date, there are two main strategies for the synthesis of enantiopure α-hydroxysilane:（1） nucleophilic addition with chiral reagent as the substrate.（2） As an alternative synthetic method, the catalytic asymmetric method is considered to be the most appealing. However, the efficient methodology with broad substrate scope in the catalytic asymmetric synthesis of α-hydroxysilanes remains rare. Thus, the development of catalytic asymmetric method for the synthesis of optically active α-hydroxysilanes is highly desirable.2 In connection with our focus on investigating the new synthetic methods, we recently questioned whether it might be possible to direct activate acylsilanes through organocatalysis because acylsilanes can be considered as an aldehyde equivalent. From a synthetic point of view, the direct activation of unactivated acylsilanes is great challenge for organocatalytic asymmetric aldol reaction. To address this issue, a new activation model for acylsilanes is required. In this context, a novel activation model for acylsilanes was developed and realized by organocatalyzed direct aldol reaction of silyl glyoxylates and aldehydes.

关键词： organocatalysis aldol reaction silyl glyoxylates acylsilanes α-hydroxysilanes

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