期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 37, 页码 11947-11951出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806059
关键词
alkyl azides; C-H amination; homogeneous catalysis; iron; porphyrinoids
资金
- State Key Laboratory of Synthetic Chemistry
- Hong Kong Research Grants Council [HKU 17303815, 17301817]
- National Key Basic Research Program of China [2013CB834802]
- Basic Research Program of Shenzhen [JCYJ20160229123546997, JCYJ20170412140251576, JCYJ20170818141858021]
Metal-catalyzed intramolecular C-H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp(3))-H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C-H bonds with up to 95% yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivi\ty at C4 or C5 could be tuned by modifying the reactivity of the C5-H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.
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