Journal
SCIENCE
Volume 353, Issue 6304, Pages 1144-1147Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaf8713
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Funding
- NIH [HL034300, HL111392, DK038226, R01 GM-114609-01]
- Robert A. Welch Foundation [I-0011, C-1764]
- Rice University
- NSF [CAREER: SusChEM CHE-1455335]
- American Chemical Society Petroleum Research Fund [51707-DNI1]
- Amgen
- Biotage
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1546097] Funding Source: National Science Foundation
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Primary and N-alkyl arylamine motifs are key functional groups in pharmaceuticals, agrochemicals, and functional materials, as well as in bioactive natural products. However, there is a dearth of generally applicable methods for the direct replacement of aryl hydrogens with NH2/NH(alkyl) moieties. Here, we present a mild dirhodium-catalyzed C-H amination for conversion of structurally diverse monocyclic and fused aromatics to the corresponding primary and N-alkyl arylamines using NH2/NH(alkyl)-O-(sulfonyl) hydroxylamines as aminating agents; the relatively weak RSO2O-N bond functions as an internal oxidant. The methodology is operationally simple, scalable, and fast at or below ambient temperature, furnishing arylamines in moderate-to-good yields and with good regioselectivity. It can be readily extended to the synthesis of fused N-heterocycles.
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