Padmanabha V Kattamuri1,2, Jun Yin1, Surached Siriwongsup1, Doo-Hyun Kwon3, Daniel H Ess3, Qun Li2, Guigen Li2,4, Muhammed Yousufuddin5, Paul F Richardson6, Scott C Sutton6, László Kürti1. 1. Department of Chemistry, Rice University, BioScience Research Collaborative , Houston, Texas 77005, United States. 2. Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University , Nanjing, 210093, P. R. China. 3. Department of Chemistry and Biochemistry, Brigham Young University , Provo, Utah 84602, United States. 4. Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409, United States. 5. Life and Health Sciences Department, University of North Texas at Dallas , Dallas, Texas 75241, United States. 6. Medicinal Sciences, Pfizer Worldwide Research and Development , 10770 Science Center Drive, San Diego, California 92121, United States.
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.
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 class="Chemical">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.
Authors: Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti Journal: J Org Chem Date: 2019-05-14 Impact factor: 4.354
Authors: Srinivasa Rao Manne; Anamika Sharma; Andrius Sazonovas; Ayman El-Faham; Beatriz G de la Torre; Fernando Albericio Journal: ACS Omega Date: 2022-02-09