141998-92-7Relevant academic research and scientific papers
N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis
Boelke, Andreas,Kuczmera, Thomas J.,Lork, Enno,Nachtsheim, Boris J.
supporting information, p. 13128 - 13134 (2021/08/09)
This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF3.
Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species
L'Helgoual'ch, Jean-Martial,Seggio, Anne,Chevallier, Floris,Yonehara, Mitsuhiro,Jeanneau, Erwann,Uchiyama, Masanobu,Mongin, Florence
, p. 177 - 183 (2008/09/17)
(Equation Presented) Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzo[b]furan, N-Boc-protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl2·TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpipe
SYNTHESIS AND REACTION OF TRIBUTYLSTANNYLPYRAZOLES
Sakamoto, Takao,Shiga, Futoshi,Uchiyama, Daishi,Kondo, Yoshinori,Yamanaka, Hiroshi
, p. 813 - 818 (2007/10/02)
1,3-Dipolar cycloaddition reaction of diazomethane and ethyl diazoacetate with tributylstannylacetylenes occurred regioselectively to afford the corresponding 3(5)-tributylstannylpyrazoles.The cycloaddition reaction of 3-phenylsydnone with the stannylacetylenes proceeded also regioselectively, and 3-tributylstannyl-1-phenylpyrazoles were isolated. 4-Tributylstannyl- and 5-tributylstannyl-1-phenylpyrazole were prepared by the stannylation of 4-lithio- and 5-lithio-1-phenylpyrazoles with tributylstannyl chloride.Iodination, benzoylation, and phenylation of the stannylpyrazoles were examined.
