- Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation
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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.
- 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
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supporting information
p. 11184 - 11196
(2017/08/21)
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- Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate
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A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.
- Sivan, Akhil,Deepthi, Ani
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supporting information
p. 1890 - 1893
(2014/03/21)
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- CHEMISTRY OF NITRO ESTERS XVII. METHOD FOR THE PRODUCTION OF MESOXALIC ESTERS
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A new preparative method was developed for the production of mesoxalic esters from bromomalonic esters and silver nitrate
- Kochergin, P. M.,Titkova, R. M.
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p. 1042 - 1044
(2007/10/02)
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