65001-45-8Relevant academic research and scientific papers
Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines
Zhang, Hong-Yu,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
supporting information, p. 4101 - 4104 (2015/03/30)
A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is
Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides
Brucelle, Fran?ois,Renaud, Philippe
, p. 3048 - 3051 (2012/08/14)
A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by oxidation with manganese dioxide.
Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst
Yang, Kai,Qiu, Yatao,Li, Zheng,Wang, Zhaoyang,Jiang, Sheng
experimental part, p. 3151 - 3159 (2011/06/23)
Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.
Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines
Utsunomiya, Masaru,Miyamoto, Yoshiki,Lpposhi, Junji,Ohshima, Takashi,Mashima, Kazushi
, p. 3371 - 3374 (2008/02/12)
A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.
Novel strategies for the solid phase synthesis of substituted indolines and indoles
Nicolaou,Roecker,Hughes, Robert,Van Summeren, Ruben,Pfefferkorn, Jeffrey A.,Winssinger, Nicolas
, p. 465 - 476 (2007/10/03)
Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process.
