683246-77-7Relevant articles and documents
Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids
Wang, Lu,Lu, Chengrong,Yue, Yanni,Feng, Chao
, p. 3514 - 3517 (2019/05/16)
A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.
Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
Yoo, Huen Ji,Youn, So Won
supporting information, p. 3422 - 3426 (2019/05/10)
A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.
Iridium-Catalyzed Highly Regioselective Azide-Ynamide Cycloaddition to Access 5-Amido Fully Substituted 1,2,3-Triazoles under Mild, Air, Aqueous, and Bioorthogonal Conditions
Song, Wangze,Zheng, Nan
, p. 6200 - 6203 (2017/11/24)
A highly regioselective method to access 5-amido fully substituted 1,2,3-triazoles by iridium-catalyzed azide-ynamide cycloaddition under mild, air, aqueous, and bioorthogonal conditions is reported. The excellent regioselectivities may derive from the strong coordination between the carbonyl oxygen of ynamide and the -acidic iridium. Since the iridium ion is insensitive to oxygen/water and exhibits low cytotoxicity, it could catalyze this reaction in both organic and biological environments efficiently. Preparation in gram-scale and application in carbohydrates highlight this method.
Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of α-allyl-tetrasubstituted-enamides
Lingua, Hugo,Vibert, Fran?ois,Mouysset, Dominique,Siri, Didier,Bertrand, Michèle P.,Feray, Laurence
, p. 3415 - 3422 (2017/06/01)
The iron(II) chloride- and copper(I) iodide-mediated carbozincation of a panel of substituted ynamides is described in this article. The reaction is totally regio- and stereoselective. Experiments showed that the reaction mediated with Fe(II) was more substrate dependent than the reaction performed with Cu(I). Interestingly, in the presence of allylbromide, stereoselective carboallylation can be achieved for the first time in a one-pot procedure, leading to skipped dienamides.
Addition of selenium(II) bromide to arylalkynylamides - a route to hypervalent T-shaped 10-Se-3 systems
Paegle, Edgars,Belyakov, Sergey,Kirsch, Gilbert,Arsenyan, Pavel
, p. 4554 - 4557 (2015/06/30)
Abstract A route for the generation of hypervalent T-shaped 10-Se-3 systems is described involving an interaction between in situ prepared selenium(II) bromide and an aryl alkynyl amide derivative. The existence of hypervalent selenium in both the solid and solution states has been supported by X-ray analysis and 77Se NMR data.
N-Substitution dependent stereoselectivity switch in palladium catalyzed hydroalkynylation of ynamides: A regio and stereoselective synthesis of ynenamides
Dwivedi, Vikas,Hari Babu, Madala,Kant, Ruchir,Sridhar Reddy, Maddi
, p. 14996 - 14999 (2015/10/12)
A highly general palladium catalysed regioselective hydroalkynylation of ynamides for versatile enamide building blocks with an alkyne tether is achieved with an N-substitution dependent stereoselectivity switch under very mild reaction conditions.
Convenient and practical alkynylation of heteronucleophiles with copper acetylides
Theunissen, Cedric,Lecomte, Morgan,Jouvin, Kevin,Laouiti, Anouar,Guissart, Celine,Heimburger, Jeremy,Loire, Estelle,Evano, Gwilherm
, p. 1157 - 1166 (2014/05/20)
Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale. Georg Thieme Verlag Stuttgart, New York.
Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato, Akihiro H.,Ohashi, Kazuhiro,Iwasawa, Tetsuo
, p. 1309 - 1311 (2013/03/13)
A facile approach to (E)-α-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues.
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
Copper-catalyzed alkynylation of amides with potassium alkynyltrifluoroborates: A room-temperature, base-free synthesis of ynamides
Jouvin, Kevin,Couty, Francois,Evano, Gwilherm
supporting information; experimental part, p. 3272 - 3275 (2010/10/21)
(Figure Presented) An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.
