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Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formation

Given 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 method...

Authors:   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 Kürti
Journal:   Journal of the American Chemical Society
Year:   2017
DOI:   10.1021/jacs.7b05279
Publication date:   13-Jul-2017
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