18676-68-1Relevant academic research and scientific papers
Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates
Le Fouler, Vincent,Duret, Guillaume,Bisseret, Philippe,Blanchard, Nicolas
, p. 3349 - 3352 (2018)
Ynamides are versatile 3-atoms building blocks for organic synthesis as they participate in a variety of ionic, radical and pericyclic processes. Converting ynamides into 5-atom building blocks, such as the yet unreported N-vinyl ynamides, would open new avenues in this fascinating chemistry. We describe herein our efforts towards such goal and demonstrate that the cross-coupling between N-vinyl carbamates and bromo-alkynes using copper(I) thiophene carboxylate, 1,10-phenanthroline and tBuOK in DMSO is a reactive system with an improved profile compared to the classical ynamides syntheses. The advantages and limitations of this copper-mediated reaction are discussed.
Directed Nickel-Catalyzed pseudo-Anomeric C?H Alkynylation of Glycals as an Approach towards C-Glycoconjugate Synthesis
de Robichon, Morgane,Branquet, David,Uziel, Jacques,Lubin-Germain, Nadège,Ferry, Angélique
, p. 5138 - 5148 (2021/09/22)
The synthesis of complex C-glycoconjugates is presented here using a key directed nickel-catalyzed C?H alkynylation step. Thanks to a bidentate amidoquinoline-type directing group, the insertion of diverse alkynyl moieties onto the pseudo-anomeric position of glycal substrates was performed on ten examples in moderate to good yields. These platforms were used as starting substrates in a click reaction with complex azides to form original C-glycoconjugates. By this route, a C-glycosylated amino acid, a C-linked disaccharide and a C-glycosylated biotin derivative were synthesized. Preliminary conditions to remove the directing group are also proposed. (Figure presented.).
Direct Assembly of Polysubstituted Propiolamidinates via Palladium-Catalyzed Multicomponent Reaction of Isocyanides
Li, Meng,Fang, Songjia,Zheng, Jia,Jiang, Huanfeng,Wu, Wanqing
supporting information, p. 8439 - 8443 (2019/10/16)
A straightforward approach for the assembly of different polysubstituted propiolamidnates via palladium-catalyzed multicomponent reaction of isocyanides, haloalkynes, and amines has been reported in which the C(sp)-C(sp2) and C(sp2)a
Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group
Pan, Rui,Shi, Cong,Zhang, Dongquan,Tian, Yang,Guo, Songjin,Yao, Hequan,Lin, Aijun
supporting information, p. 8915 - 8920 (2019/11/14)
An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.
