Novel strategies for the solid phase synthesis of substituted indolines and indoles
摘要:
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. (C) 2002 Elsevier Science Ltd. All rights reserved.
Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
作者:Jiaming Li、Robert H. Grubbs、Brian M. Stoltz
DOI:10.1021/acs.orglett.6b02722
日期:2016.11.4
A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.
Palladium(II)-Catalyzed Oxidative Cascade Cyclization Reactions of Anilides and Anilines: Scope and Mechanistic Investigations
作者:Kai-Tai Yip、Dan Yang
DOI:10.1002/asia.201100242
日期:2011.8.1
catalyst system and molecular oxygen as a green oxidant, acrylanilides and N‐allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylanilides of different substitution patterns on olefinic units. Mechanistic studies revealed that cyclization of acrylanilides proceeded through an intramolecular syn‐amidopalladation pathway. The