ja7b05279_si_001.pdf (29.95 MB)
Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formation
journal contribution
posted on 2017-06-26, 00:00 authored by Padmanabha
V. Kattamuri, Jun Yin, Surached Siriwongsup, Doo-Hyun Kwon, Daniel H. Ess, Qun Li, Guigen Li, Muhammed Yousufuddin, Paul F. Richardson, Scott C. Sutton, László KürtiGiven
the importance of amines in a large number of biologically
active natural products, active pharmaceutical ingredients, agrochemicals,
and functional materials, the development of efficient C–N
bond-forming methods with wide substrate scope continues to be at
the frontier of research in synthetic organic chemistry. Here, we
present a general and fundamentally new synthetic approach for the
direct, transition-metal-free preparation of symmetrical and unsymmetrical
diaryl-, arylalkyl-, and dialkylamines that relies on
the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable
electrophilic aminating agents. Practical single and double
polarity reversal (i.e., umpolung) of the nitrogen atom is achieved
using sterically and electronically tunable ketomalonate-derived
imines and oximes. Overall, this novel approach represents an operationally
simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed
C–N cross-coupling methods that are currently used to access
structurally diverse secondary amines.
History
Usage metrics
Categories
Keywords
bond-formingalternativepolaritydialkylingredientmaterialscalableoximereversalSustainablesubstratearylumpolungPlatformNewfrontierresearchaccessFormationapproachmethodDoubly Electrophilic Aminating Agentsimportancei.eketoscopeunsymmetricalagrostericallyiminetransition-metal-catalyzedaminesnitrogen atomcross-couplingdiaryltransition-metal-freetunablepreparationagentaminatingelectroPracticalbench-stableBondSinglynucleo
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC