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.
Skeletally Tunable Seven-Membered-Ring Fused Pyrroles
Andreou, Dimitrios,Essien, Nsikak B.,Pubill-Ulldemolins, Cristina,Terzidis, Michael A.,Papadopoulos, Athanasios N.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information, p. 6685 - 6690 (2021/09/11)
We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.
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.
Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
Mimura, Shohei,Mizushima, Sho,Sawamura, Masaya,Shimizu, Yohei
supporting information, p. 537 - 543 (2020/05/14)
A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.
