2216-94-6Relevant articles and documents
On the synthesis of arylpropiolic acids and investigations towards the formation of vinyl chlorides by HCl addition during esterification reactions
Hapke, Marko,Kral, Karolin,Spannenberg, Anke
, p. 642 - 652 (2011)
The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl2 was examined. Georg Thieme Verlag Stuttgart New York.
Facile Dehydration of Activated Ketones to Alkynes
Hendrickson, James B.,Hussoin, Md. Sajjat
, p. 217 - 218 (1989)
Ketones activated by β-carbonyl or phenyl groups are readily dehydrated to alkynes with (PhP(1+))2O, 2OTf(1-) and triethylamine in refluxing 1,2-dichloroethane.
Palladium-catalyzed coupling of alkynes with chloroformates to form alkynecarboxylic acid esters
Boettcher, Arnd,Becker, Heike,Brunner, Melanie,Preiss, Thomas,Henkelmann, Jochem,De Bakker, Christel,Gleiter, Rolf
, p. 3555 - 3556 (1999)
The preparation of alkynecarboxylic acid esters, which are versatile building blocks for the synthesis of heterocyclic compounds, is described by means of the, palladium-catalyzed coupling of alkynes with chloroformates for the first time. The Royal Society of Chemistry 1999.
trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines
Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan
supporting information, (2021/10/04)
trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.
De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions
Wang, Dan,Lin, Junhui,Zhu, Yannan,Huang, You
supporting information, p. 1873 - 1877 (2021/02/16)
The robustness of phosphine catalysis enabling the domino benzannulation reactions of allenoates with enamines is described. A broad array of substituted terephthalates were delivered under simple and practical reaction conditions. Furthermore, the reaction could be carried out on a gram scale with higher yield, and various conversions of the terephthalate products demonstrate the versatility of this transformation. (Figure presented.).
Ynamide-Mediated Intermolecular Esterification
Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
, p. 6188 - 6194 (2020/05/26)
An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.
