38238-96-9Relevant academic research and scientific papers
Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones
Pal, Arpal,Koduri, Naga D.,Wang, Zhiguo,Quiroz, Erika Lopez,Chong, Alexandra,Vuong, Matthew,Rajagopal, Nisha,Nguyen, Michael,Roberts, Kenneth P.,Hussaini, Syed R.
, p. 586 - 589 (2017)
The development of operationally simple and cost-effective methods for C[sbnd]C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, α-diazoketosulfones and α-diazomonoketones.
Triflate/mesylate ratios and competing C-O and S-O bond cleavages in nucleophilic vinylic substitution
Schottland, Ettie Z.,Rappoport, Zvi
, p. 8536 - 8543 (2007/10/03)
In an attempt to develop the kOTf/kOMs ratio as a mechanistic tool for the "addition-elimination" route in nucleophilic vinylic substitution, several pairs of vinyl mesylates and triflates were prepared. Whereas reactions of ArC(LG)=C(CO2Et)2 (LG = OTf, OMs) with piperidine and morpholine in MeCN or THF gave the normal substitution product with kOTf/kOMs ratios of 4.3-10.6, the reaction of the mesylates, Ar = p-O2NC6H4, and of PhC(OMs)=C(Me)CN with MeS- gave a ketone via an S-O bond cleavage. A related mesityl-substituted tosylate also reacted with p-MeC6H4X- (X = O, S) via an S-O bond cleavage. Hence, kOTf/kOMs ratios cannot be used as a general mechanistic tool. Several reactivity ratios in vinylic substitution are briefly discussed.
