54888-61-8Relevant academic research and scientific papers
Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
Black, Gary W.,Brancale, Andrea,Castagnolo, Daniele,Colonna, Serena,Ferla, Salvatore,Masci, Domiziana,Turner, Nicholas J.,Varricchio, Carmine,Zhao, Fei
, p. 6414 - 6421 (2020/07/09)
The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.
Mononuclear complexes of a tridentate redox-active ligand with sulfonamido groups: Structure, properties, and reactivity
Cook, Sarah A.,Bogart, Justin A.,Levi, Noam,Weitz, Andrew C.,Moore, Curtis,Rheingold, Arnold L.,Ziller, Joseph W.,Hendrich, Michael P.,Borovik
, p. 6540 - 6547 (2018/08/16)
The design of molecular complexes of earth-abundant first-row transition metals that can catalyze multi-electron C-H bond activation processes is of interest for achieving efficient, low-cost syntheses of target molecules. To overcome the propensity of these metals to perform single-electron processes, redox-active ligands have been utilized to provide additional electron equivalents. Herein, we report the synthesis of a novel redox active ligand, [ibaps]3-, which binds to transition metals such as FeII and CoII in a meridional fashion through the three anionic nitrogen atoms and provides additional coordination sites for other ligands. In this study, the neutral bidentate ligand 2,2′-bipyridine (bpy) was used to complete the coordination spheres of the metal ions and form NEt4[MII(ibaps)bpy] (M = Fe (1) or Co (1-Co)) salts. The FeII salt exhibited rich electrochemical properties and could be chemically oxidized by 1 and 2 equiv. of ferrocenium to form singly and doubly oxidized species, respectively. The reactivity of 1 towards intramolecular C-H bond amination of aryl azides at benzylic and aliphatic carbon centers was explored, and moderate to good yields of the resulting indoline products were obtained.
Kinetic resolution of indolines through reductive amination of aldehydes by chiral Br?nsted acid
Wang, Yingwei,Li, Guangxun,Liu, Hongxin,Tang, Zhuo,Cao, Yuan,Zhao, Gang
supporting information, p. 2993 - 2996 (2017/07/07)
We have developed a highly efficient and practical strategy for the kinetic resolution of indoline derivatives, involving a chiral Br?nsted acid-catalyzed iminium ion formation and asymmetric transfer hydrogenation cascade process. The kinetic resolution allows the synthesis of 2-substituted N-benzylindolines in good yields with moderate to excellent enantioselectivities.
Cobalt catalyzed sp3 C-H amination utilizing aryl azides
Villanueva, Omar,Weldy, Nina MacE,Blakey, Simon B.,MacBeth, Cora E.
, p. 6672 - 6675 (2015/10/28)
A dinuclear Co(ii) complex supported by a modular, tunable redox-active ligand system is capable of selective C-H amination to form indolines from aryl azides in good yields at low (1 mol%) catalyst loading. The reaction is tolerant of medicinally relevant heterocycles, such as pyridine and indole, and can be used to form 5-, 6-, and 7-membered rings. The synthetic versatility obtained using low loadings of an earth abundant transition metal complex represents a significant advance in catalytic C-H amination technology.
