38328-16-4Relevant articles and documents
Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation
Zhang, Yu-Lan,Yang, Lei,Wu, Jie,Zhu, Chunyin,Wang, Peng
, p. 7768 - 7772 (2020/10/09)
Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl rad
Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate
Cao, Zhi-Chao,Xu, Pei-Lin,Luo, Qin-Yu,Li, Xiao-Lei,Yu, Da-Gang,Fang, Huayi,Shi, Zhang-Jie
supporting information, p. 781 - 785 (2019/06/24)
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.
Borata-Wittig olefination reactions of ketones, carboxylic esters and amides with bis(pentafluorophenyl)borata-alkene reagents
Wang, Tongdao,Kohrt, Sonja,Daniliuc, Constantin G.,Kehr, Gerald,Erker, Gerhard
supporting information, p. 6223 - 6232 (2017/08/02)
The strongly electrophilic borane derivative amino-CH2CH2CH2-B(C6F5)26 was α-CH deprotonated with LiTMP to give the borata-alkene {[amino-(CH2)2-CHB(C6F5)2-][Li+]}29 which underwent facile [2 + 2] cycloaddition reactions with benzophenone or fluorenone to yield the respective 1,2-oxaboretanides 11a,b. Compounds 9 and 11 were characterized by the X-ray diffraction. Thermolysis or hydrolysis of compounds 11a,b gave the corresponding borata-Wittig olefination products 12a,b. A variety of R-CH2-CH2-B(C6F5)2 boranes (conveniently generated by hydroboration of terminal alkenes R-CHCH2 with Piers' borane [HB(C6F5)2]) were analogously deprotonated to give the respective borata-alkenes 16a-e (R: Ph-CH2-, nC4H9, tBu, Cy, PhCH2CH2-). They underwent "non-classical" borata-Wittig olefination reactions with ethylformate to give the respective enolether carbonylation products, or their C1-elongated aldehydes (after hydrolysis). The borata-alkene [Ph-(CH2)2-CHB(C6F5)2-] [Li+HTMP] (16a) gave the respective "non-classical" borata-Wittig olefination products, the enolethers 25a,b and 27, respectively, upon treatment with methyl- or ethyl acetate or γ-butyrolactone.