Practical Singly and Doubly Electrophilic Aminating Agents

A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation

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

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

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 methods that are currently used to access structurally diverse secondary amines.

Original languageEnglish (US)
Pages (from-to)11184-11196
Number of pages13
JournalJournal of the American Chemical Society
Volume139
Issue number32
DOIs
StatePublished - Aug 16 2017

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Amines
Transition metals
Nitrogen
Carbon
Metals
Organic Chemistry
Agrochemicals
Atoms
Nucleophiles
Imines
Oximes
Functional materials
Biological Products
Drug products
Substrates
Research
Pharmaceutical Preparations
mesoxalic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Practical Singly and Doubly Electrophilic Aminating Agents : A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation. / Kattamuri, Padmanabha V.; Yin, Jun; Siriwongsup, Surached; Kwon, Doo Hyun; Ess, Daniel H.; Li, Qun; Li, Guigen; Yousufuddin, Muhammed; Richardson, Paul F.; Sutton, Scott C.; Kürti, László.

In: Journal of the American Chemical Society, Vol. 139, No. 32, 16.08.2017, p. 11184-11196.

Research output: Contribution to journalArticle

Kattamuri, PV, Yin, J, Siriwongsup, S, Kwon, DH, Ess, DH, Li, Q, Li, G, Yousufuddin, M, Richardson, PF, Sutton, SC & Kürti, L 2017, 'Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation', Journal of the American Chemical Society, vol. 139, no. 32, pp. 11184-11196. https://doi.org/10.1021/jacs.7b05279
Kattamuri, Padmanabha V. ; Yin, Jun ; Siriwongsup, Surached ; Kwon, Doo Hyun ; Ess, Daniel H. ; Li, Qun ; Li, Guigen ; Yousufuddin, Muhammed ; Richardson, Paul F. ; Sutton, Scott C. ; Kürti, László. / Practical Singly and Doubly Electrophilic Aminating Agents : A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 32. pp. 11184-11196.
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