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Fluoroalkyl N-sulfonyl hydrazones:An efficient reagent for the synthesis of fluoroalkylated compounds

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Science China Chemistry 2021年第10期64卷 1614-1629页

作者： paramasivam Sivagur Xihe Bi Department of Chemistry Northeast Normal UniversityChangchun 130024China

Fluoroalkyl N-sulfonyl hydrazones are versatile reagents that can be used to synthesize a wide range of diverse fluoroalkylated organic *** it has been known since 1975,the chemistry of fluoroalkyl N-sulfonyl hydrazones has recently only received great attention from the scientific ***,they are used as either safe and bench-stable diazo precursors in carbene transfer reactions or as 1,3-dipoles in cycloaddition and cyclization ***,fluoroalkyl N-sulfonyl hydrazones to replace toxic fluoroalkyl diazo compounds in carbene transfer reactions reduce the risk of rapid accumulation of explosive diazo compounds and improve functional group compatibility and substrate *** the growing importance of fluoroalkyl N-sulfonyl hydrazones in chemical synthesis,a comprehensive review of this topic in the literature is essential to demonstrate their synthetic *** this review,we critically summarize and comprehensively analyze the publications in various literatures on the chemistry of fluoroalkyl N-sulfonyl hydrazones starting from 1990 to *** classification of the different reactivity profiles of fluoroalkyl N-sulfonyl hydrazones and the efficiencies of similar types of reactions or substrates with fluoroalkyl diazo compounds are compared.

关键词： An efficient reagent for the synthesis of fluoroalkylated compounds Fluoroalkyl N-sulfonyl hydrazones

[4+1]Annulation of in situ generated azoalkenes with amines:A powerful approach to access 1-substituted 1,2,3-triazoles

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Chinese Chemical Letters 2022年第3期33卷 1550-1554页

作者： Hongwei Wang Yongquan Ning paramasivam sivaguru Giuseppe Zanoni Xihe Bi Department of Chemistry Northeast Normal UniversityChangchun 130024China Department of Chemistry University of PaviaViale Taramelli 12Pavia 27100Italy State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

1-Substituted 1,2,3-triazoles represents‘privileged’structural scaffolds of many clinical ***,the traditional methods for their preparation mainly rely on thermal[3+2]cycloaddition of potentially dangerous acetylene and *** we report a base-mediated[4+1]annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones(DFHZ-Ts)with amines under relatively mild *** azide-and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific *** transformation has great functional group tolerance and can suit a broad substrate ***,the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality,practicability and applicability.

关键词： [4+1]Annulation Azoalkene Late-stage functionalization 1-Substituted 1 2 3-triazoles

Neighbouring carbonyl group-assisted sequential 1,2-azide and1,4-oxygen migrations of vinyl azides leading to α-azido ketones

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Science China Chemistry 2020年第4期63卷 460-466页

作者： Yi Gai Yongquan Ning paramasivam sivaguru Xiaomeng Li Yue Zhao Jiayi Wu Xihe Bi Department of Chemistry Northeast Normal UniversityChangchun 130024China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

The development of azide migration reactions is a formidable challenge due to potential competition from side processes driven by the release of molecular nitrogen. Here, we show a novel neighbouring carbonyl group-assisted sequential 1,2-azide and 1,4-oxygen migration reaction of α-vinyl azides for the efficient preparation of a range of α-azido ketones. This represents the first transformation of α-vinyl azides into α-azido ketones. Notable features of this method are its high efficiency, broad substrate scope, excellent functional group compatibility, and high yields. The computational studies gave a key insights into the regioselective 1,2-azide and 1,4-oxygen migrations assisted by the neighbouring carbonyl group. Further conversions into a variety of nitrogen-containing compounds demonstrated the synthetic utility of the α-azido ketone products. Preliminary mechanistic studies disclosed a novel reaction mechanism involving neighbouring carbonyl group-assisted sequential 1,2-azide and1,4-oxygen migrations.

关键词： vinyl azide azide migration neighboring carbonyl group-assisted PhIF2 α-azido ketones