期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 32, 页码 11184-11196出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05279
关键词
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资金
- Rice University
- National Institutes of Health [R01 GM-114609-01, R33 DA031860]
- National Science Foundation [CAREER: SusChEM CHE-1546097]
- Robert A. Welch Foundation [C-1764]
- Amgen
- Biotage
- ICBMS/Nanjing University
- National Science Foundation of China (NSFC) [21332005, 21672100]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1546097] Funding Source: National Science Foundation
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.
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