49572-59-0Relevant 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.
, p. 13128 - 13134 (2021)
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.
NMR Quantification of Halogen-Bonding Ability to Evaluate Catalyst Activity
Chang, Yun-Pu,Tang, Teresa,Jagannathan, Jake R.,Hirbawi, Nadia,Sun, Shaoming,Brown, Jonah,Franz, Annaliese K.
supporting information, p. 6647 - 6652 (2020/09/09)
Quantification of halogen-bonding abilities is described for a series of benzimidazolium-, imidazolium- and bis(imidazolium) halogen-bond donors (XBDs) using 31P NMR spectroscopy. The measured Δδ(31P) values correlate with calculated activation free energ
2-halogenoimidazolium salt catalyzed aza-diels-alder reaction through halogen-bond formation
Takeda, Youhei,Hisakuni, Daichi,Lin, Chun-Hsuan,Minakata, Satoshi
, p. 318 - 321 (2015/01/30)
2-Halogenoimidazolium salts are found to catalyze aza-Diels-Alder reaction of aldimines with Danishefsky diene in an efficient manner. Comparative studies and titration experiments support the formation of halogen bonding between imines and catalysts.
Synthesis and optical properties of 2,2'-biimidazole and benzo[d]imidazole derivatives: Changing π-conjugation by photoexcitation
Matsumoto, Shoji,Zhao, Yu,Akazome, Motohiro
, p. 261 - 273 (2014/01/17)
1,1',5,5'-Tetraaryl-2,2'-biimidazole and benzo[d]imidazole derivatives were synthesized. Symmetrical and unsymmetrical benzo[d]imidazole derivatives could be obtained by the Pd-catalyzed coupling reaction between 2-iodo-benzo[d] imidazole and the correspo
Copper-mediated trifluoromethylation of heteroaromatic compounds by trifluoromethyl sulfonium salts
Zhang, Cheng-Pan,Wang, Zong-Ling,Chen, Qing-Yun,Zhang, Chun-Tao,Gu, Yu-Cheng,Xiao, Ji-Chang
supporting information; experimental part, p. 1896 - 1900 (2011/04/16)
Copper is king! A convenient method for the synthesis of trifluoromethylated heteroaromatic compounds under mild conditions has been developed based on the observation that 1 can be reduced by certain metals (see scheme). Substrate 1 is assumed to be reduced by copper via a single-electron transfer mechanism, and CuCF3 is the most probable intermediate in this reaction. DMF=N,N-dimethylformamide, Tf=triflate.
