16497-41-9Relevant articles and documents
A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events
Beard, Matthew C.,Chen, Xihan,Han, Chuang,Lin, Yixiong,Martin, Jovan San,Miller, Collin,Wang, Xiaoming,Yamamoto, Nobuyuki,Yan, Yanfa,Yan, Yong,Yazdi, Sadegh,Zeng, Xianghua
supporting information, p. 11361 - 11369 (2021/08/16)
Heterogeneous photocatalysis is less common but can provide unique avenues for inducing novel chemical transformations and can also be utilized for energy transductions, i.e., the energy in the photons can be captured in chemical bonds. Here, we developed a novel heterogeneous photocatalytic system that employs a lead-halide perovskite nanocrystal (NC) to capture photons and direct photogenerated holes to a surface bound transition metal Cu-site, resulting in a N-N heterocyclization reaction. The reaction starts from surface coordinated diamine substrates and requires two subsequent photo-oxidation events per reaction cycle. We establish a photocatalytic pathway that incorporates sequential inner sphere electron transfer events, photons absorbed by the NC generate holes that are sequentially funneled to the Cu-surface site to perform the reaction. The photocatalyst is readily prepared via a controlled cation-exchange reaction and provides new opportunities in photodriven heterogeneous catalysis.
Electrochemical Conversion of Phthaldianilides to Phthalazin-1,4-diones by Dehydrogenative N?N Bond Formation
Kehl, Anton,Gieshoff, Tile,Schollmeyer, Dieter,Waldvogel, Siegfried R.
supporting information, p. 590 - 593 (2017/12/26)
The electrochemical synthesis of 6-membered rings via anodic dianilide N?N coupling is challenging due to concurring benzoxazole co-formation. The rigidity of the a phthalic acid backbone allows a novel access to phthalazin-1,4-diones by N?N bond formation using anodically generated amidyl radicals. Since conventional synthetic routes to phthalazin-1,4-diones require the use of toxic N,N′-diarylhydrazines and generate reagent waste, a safer and more sustainable approach is required. Easy accessible starting materials, a broad scope of applicable functional groups, promising yields, and a very simple set-up elevate this sustainable method.
Variable Regioselectivity in Reactions of N-Lithio-N-vinylaniline with Arenedicarboxylates and α,β-Unsaturated Esters
Katrizky, Alan R.,Oniciu, Daniela C.,Mancheno, Balbino,Barcolk, Richard A.
, p. 113 - 119 (2007/10/02)
Regioselectivity patterns for the reactions of N-lithio-N-vinylaniline with several arenedicarboxylates and esters of α,β-unsaturated esters are reported.N-Lithio-N-vinylaniline reacted at both of its ambient anionic sites, to give β-enamino ketones and amide derivatives.A bridgehead compound resulting from cycloaddition involving N-lithio-N-vinylaniline was also formed in the reactions with ethyl cinnamate and ethyl phenylpropiolate.The structures of all compounds formed were fully characterized by NMR techniques.
