1174523-94-4Relevant articles and documents
Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides
Donnard, Morgan,Golling, Stéphane,Leroux, Frédéric R.
, p. 8093 - 8097 (2021/10/25)
In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and mor
Ligand-Controlled Regiodivergent Hydroformylation of Ynamides: A Stereospecific and Regioselective Access to 2- And 3-Aminoacroleins
Wagner, Patrick,Donnard, Morgan,Girard, Nicolas
supporting information, p. 8861 - 8866 (2019/11/03)
The rhodium-catalyzed hydroformylation of ynamides is described and gives selective access to 2- or 3-aminoacrolein derivatives. The regioselectivity of this carbonylation can be completely controlled at will thanks to the nature of the ligand used. This represents the first example of regiodivergent alkyne hydroformylation. The influence of the substituents on the different positions of the ynamide has been investigated, and it appears that this reaction is tolerant to a wide range of functional groups.
Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides
Baldassari, Lucas L.,de la Torre, Aurélien,Li, Jing,Lüdtke, Diogo S.,Maulide, Nuno
supporting information, p. 15723 - 15727 (2017/12/02)
A novel ynamide preactivation strategy enables the use of otherwise incompatible reagents and allows preparation of α,β-disubstituted enamides with high regio- and stereoselectivity. Mechanistic analysis reveals the intermediacy of a triflate-bound intermediate as a solution-stable, effective keteniminium reservoir, whilst still allowing subsequent addition of organometallic reagents.
Efficient and recyclable Cu2(BDC)2(BPY)-catalyzed oxidative amidation of terminal alkynes: Role of bipyridine ligand
Le, Hanh T. N.,Tran, Thuan V.,Phan, Nam T. S.,Truong, Thanh
, p. 851 - 859 (2015/02/19)
We have described an efficient method for oxidative cross coupling reactions between activated N-H amines and terminal alkynes using heterogeneous Cu2(BDC)2(BPY) as recyclable catalyst (BDC = benzene-1,4-dicarboxylate; BPY = 4,4′-bipyridine). The optimal conditions involved the use of inexpensive NaHCO3 base and oxygen as terminal oxidant in toluene solvent at 80°C. Reactions proceeds efficiently, and high selectivity with only trace amount of diynes as well as good yields were achieved in a short reaction time. The Cu2(BDC)2(BPY) exhibited excellent catalytic activity and selectivity as compared to other Cu-MOFs on a broad reaction scope. Interestingly, the presence of bipyridine ligand was shown to enhance the catalyst stability. Thus, the Cu2(BDC)2(BPY) could be facilely separated from the reaction mixture by simple centrifugation and could be reused several times with only a slight decrease in catalytic activity.
A Bronsted acid catalyzed redox arylation
Peng, Bo,Huang, Xueliang,Xie, Lan-Gui,Maulide, Nuno
supporting information, p. 8718 - 8721 (2014/08/18)
A Bronsted acid catalyzed redox arylation of ynamides that employs aryl sulfoxides as the arylating agents is reported. This metal-free transformation proceeds at room temperature and efficiently affords α-arylated oxazolidinones in a redox-neutral, atom-
Gold-catalyzed nitrene transfer to activated alkynes: Formation of α,β-unsaturated amidines
Li, Chaoqun,Zhang, Liming
supporting information; experimental part, p. 1738 - 1741 (2011/05/11)
A gold-catalyzed intermolecular nitrene transfer to alkynes was developed for the first time, revealing a new mode of nitrene transfer and providing a novel access to versatile α-imino metal carbenes. Various mild nitrene-transfer reagents were examined, and iminopyridium ylides especially those based on 3,5-dichloropyridine proved be highly effective. With activated alkynes such as N-alkynyloxazolidinones as substrates, α,β- unsaturated amidines were formed in mostly good yields.
Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers
Davies, Paul W.,Cremonesi, Alex,Martin, Nicolas
supporting information; experimental part, p. 379 - 381 (2011/02/27)
Ynamides and ynol ethers undergo intermolecular gold-catalysed reaction with a nucleophilic oxidant to access metal-carbenoid reactivity patterns. A site-specific oxidation/1,2-insertion cascade is used for a general access to functionalised α,β-unsaturat
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.
Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling
Jia, Wei,Jiao, Ning
supporting information; experimental part, p. 2000 - 2003 (2010/07/03)
Figure presented A Cu-catalyzed aerobic oxidative amidation of propiolic acids via decarboxylation under air has been developed. Only carbon dioxide is produced as byproduct in this approach. The use of air as oxidant makes this method more useful and easy to handle.
Predictable and regioselective insertion of internal unsymmetrical alkynes in rhodium-catalyzed cycloadditions with alkenyl isocyanates
Friedman, Rebecca Keller,Rovis, Tomislav
supporting information; experimental part, p. 10775 - 10782 (2009/12/25)
A regioselective, rhodium-catalyzed cycloaddition between a variety of internal, unsymmetrical alkynes is described. We document the impact of both steric and electronic properties of the alkyne on reaction course, efficiency, and enantioselectivity. The
