Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 44, Pages 18253-18256Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja309637r
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Funding
- UT Southwestern Endowed Scholars in Biomedical Research Program
- Robert A. Welch Foundation [I-1764, GL-625910]
- ACS Petroleum Research Fund [51707-DNI1]
- American Cancer Society & Simmons Cancer Center Institutional Research Grant [ACS-IRG 02-196]
- NIH [GM31278]
- BYU
- Fulton Supercomputing Lab
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Herein, we disclose the first metal-free synthesis of primary aromatic amines from arylboronic acids, a reaction that has eluded synthetic chemists for decades. This remarkable transformation affords structurally diverse primary arylamines in good chemical yields, including a variety of halogenated primary anilines that often cannot be prepared via transition-metal-catalyzed amination. The reaction is operationally simple, requires only a slight excess of aminating agent, proceeds under neutral or basic conditions, and, importantly, can be scaled up to provide multigram quantities of primary anilines. Density functional calculations reveal that the most likely mechanism involves a facile 1,2-aryl migration and that the presence of an ortho nitro group in the aminating agent plays a critical role in lowering the free energy barrier of the 1,2-aryl migration step.
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