- Direct vinylation of natural alcohols and derivatives with calcium carbide
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Vinyl ethers are essential synthetic building blocks for organic synthesis, especially for polymer synthesis and highly vinylated polyol substrates. Herein, a transition metal-free, mild, and safe protocol has been developed for direct vinylation of natural alcohols with calcium carbide. Various sugar alcohols, phenol and its derivatives were tested and proved successful using this green methodology. Selectivity of full vinylated products of the reaction decreases with increasing hydroxyl groups because of side reactions occurring under the basic medium. Electron-donating substituted phenols work more efficiently than electron-withdrawing substituted phenols in general. This methodology may provide new insights on selective vinylation of electron-rich biomass-derived materials.
- Teong, Siew Ping,Chua, Ariel Yi Hui,Deng, Shiyun,Li, Xiukai,Zhang, Yugen
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supporting information
p. 1659 - 1662
(2017/06/07)
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- Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene
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Phenols and naphthols react with acetylene in a superbasic system KOH-DMSO forming the corresponding aryl vinyl ethers in up to 80% yields.
- Trofimov,Oparina,Kolyvanov,Vysotskaya,Gusarova
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p. 188 - 194
(2015/04/14)
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- Three-component reaction between vinyl ethers, secondary phosphines, and elemental selenium: One-pot synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl phosphinodiselenoates
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A family of previously unknown phosphinodiselenoic esters containing a selenoacetal moiety, R2(=Se)SeCH(Me)OR1 (R1, R2=alkyl, aryl, etc.), were synthesized by means of a three-component reaction between the elem
- Gusarova, Nina K.,Artemev, Alexander V.,Oparina, Ludmila A.,Kolyvanov, Nikita A.,Malysheva, Svetlana F.,Vysotskaya, Oksana V.,Trofimov, Boris A.
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experimental part
p. 431 - 438
(2012/03/11)
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- Development of a highly efficient catalytic method for synthesis of vinyl ethers
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A new method for the preparation of alkyl vinyl ethers has been developed. Thus, various types of alkyl vinyl ethers were synthesized by the reaction of alcohols with vinyl acetate under the influence of a catalytic amount of [Ir(cod)Cl]2 combined with Na2CO3 in good to excellent yields. Copyright
- Okimoto, Yoshio,Sakaguchi, Satoshi,Ishii, Yasutaka
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p. 1590 - 1591
(2007/10/03)
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