1616562-91-4Relevant academic research and scientific papers
Interruption of Formal Schmidt Rearrangement/Hosomi-Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes
Fang, Guichun,Liu, Zhenhua,Cao, Shanshan,Yuan, Haiyan,Zhang, Jingping,Pan, Ling
, p. 7113 - 7116 (2018)
An interrupted Schmidt rearrangement/Hosomi-Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C-C bond formation. As a result, a variety of homoallylic/allenylic amines can be afforded in good yields under mild reaction conditions with well-defined functional-group tolerance.
AgN3-Catalyzed Hydroazidation of Terminal Alkynes and Mechanistic Studies
Bi, Xihe,Cao, Shanshan,Ji, Qinghe,Li, Huaizhi,Pang, Maolin,Yuan, Haiyan,Zhang, Jingping
supporting information, p. 7083 - 7091 (2020/05/14)
The hydroazidation of alkynes is the most straightforward way to access vinyl azides-versatile building blocks in organic synthesis. We previously realized such a fundamental reaction of terminal alkynes using Ag2CO3 as a catalyst. H
Synthesis method for preparing a large amount of alpha-vinyl azide compounds
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Paragraph 0029; 0068; 0070; 0071; 0090, (2018/07/07)
The invention relates to a synthesis method for preparing a large amount of alpha-vinyl azide compounds, and belongs to the technical field of organic synthesis chemistry. In the prior art, alpha-vinyl azide compounds have unique reactivity, the synthesis and the applications of the alpha-vinyl azide compounds are important, and the alpha-vinyl azide compounds have good application prospects in the field of organic synthesis. According to the present invention, a large amount of stereospecific alpha-vinyl azide compounds are subjected to one-step efficient synthesis by using the simple and easily-available raw material acetylene-based compound and the azidotrimethylsilane; the synthesis method has advantages of simple and easily-available raw materials, wide application, low catalyst consumption, batch synthesis, simple operation method and efficient reaction, and is suitable for synthesis of a large amount of alpha-vinyl azide compounds; and the product has the stereospecific structure.
Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines
Ning, Yongquan,Zhao, Xue-Feng,Wu, Yan-Bo,Bi, Xihe
supporting information, p. 6240 - 6243 (2017/11/24)
An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of β-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.
General silver-catalyzed hydroazidation of terminal alkynes by combining TMS-N3 and H2O: Synthesis of vinyl azides
Liu, Zhenhua,Liao, Peiqiu,Bi, Xihe
supporting information, p. 3668 - 3671 (2014/08/05)
A general hydroazidation of unactivated alkynes using silver catalysis is reported. The reactions of diverse terminal alkynes with trimethylsilyl azide (TMS-N3) in the presence of H2O afforded the corresponding vinyl azides in good to excellent yields. This reaction has a broad substrate scope, good functional group tolerance, simple operation, and high reaction efficiency, thus providing an easy access to various functionalized vinyl azides.
