Tunable, Chemoselective Amination via Silver Catalysis
摘要:
Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C H bond or add it directly to a C=C bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C H insertion by manipulating the coordination geometry of the active catalysts.
[EN] BICYCLIC METHYLENE AZIRIDINES AND REACTIONS THEREOF<br/>[FR] MÉTHYLÈNE AZIRIDINES BICYCLIQUES ET RÉACTIONS DE CELLES-CI
申请人:SCHOMAKER JENNIFER
公开号:WO2013033245A1
公开(公告)日:2013-03-07
The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.
Synthesis of Propargylic and Allenic Carbamates <i>via</i> the C–H Amination of Alkynes
作者:R. David Grigg、Jared W. Rigoli、Simon D. Pearce、Jennifer M. Schomaker
DOI:10.1021/ol203055v
日期:2012.1.6
Propargylic amines are important intermediates for the synthesis of nitrogen-containing heterocycles. The insertion of a nitrene into a propargylic C–H bond has not been explored, despite the attention directed toward the Rh-catalyzed amination of other types of C–H bonds. In this communication, the conversion of a series of homopropargylic carbamates to propargylic carbamates and aminated allenes
BICYCLIC METHYLENE AZIRIDINES AND REACTIONS THEREOF
申请人:Wisconsin Alumni Research Foundation
公开号:US20160075668A1
公开(公告)日:2016-03-17
The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.