71202-01-2Relevant academic research and scientific papers
Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
Boelke, Andreas,Nachtsheim, Boris J.
supporting information, p. 184 - 191 (2019/12/11)
The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).
Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
Murata, Chihiro,Ogura, Tetsuhiro,Narita, Shuhei,Kondo, Anna P.,Iwasaki, Natsumi,Saito, Tamao,Usuki, Toyonobu
, p. 1428 - 1433 (2016/02/19)
4-Methyl-5-pentylbenzene-1,3-diol (MPBD) is a secondary metabolite of SteelyA polyketide synthase, which controls cell aggregation and spore maturation of Dictyostelium discoideum. In this study, chemical synthesis of MPBD and its derivatives was achieved. Structure-activity relationship (SAR) studies for antimicrobial activities against Escherichia coli and Bacillus subtilis were also conducted.
Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
Jung, Youngeun,Singh, Dileep Kumar,Kim, Ikyon
supporting information, p. 2689 - 2693 (2017/01/09)
The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and S
[5]Helicenes by tandem radical cyclisation
Harrowven, David C.,Nunn, Michael I.T.,Fenwick, David R.
, p. 7345 - 7347 (2007/10/03)
A new and rapid approach to [5]helicenes is described. A central feature is the use of a sequential, non-reducing radical cyclisation reaction of (Z,Z)-1,4-bis(2-iodostyryl)benzene derivatives, viz. 3→1, mediated by tributyltin hydride.
