Synfacts 2012; 8(4): 0397
DOI: 10.1055/s-0031-1290730
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Intramolecular Allylic C−H Amination

Contributor(s):
Mark Lautens
,
Hasnain A. Malik
Paradine SM, White MC * University of Illinois, Urbana, USA
Iron-Catalyzed Intramolecular Allylic C−H Amination.

J. Am. Chem. Soc. 2012;
134: 2036-2039
Further Information

Publication History

Publication Date:
20 March 2012 (online)

 

Significance

The area of transition-metal-catalyzed C−H functionalization reactions has seen much interest from the synthetic community in the last decade. Indeed, the field continues to progress and encompass increasingly complex and difficult chemical transformations with milder conditions and cheaper precatalyst/ligand combinations. The use of an inexpensive and environmentally benign metal such as iron in such transition-metal chemistry is highly advantageous and should attract much interest in the coming years.


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Comment

The authors report an iron-catalyzed intramolecular C−H amination. A variety of systems are studied and the yields are generally moderate to good with moderate to excellent levels of diastereoselectivity. Reactivity trends are explored thoroughly and a mechanistic study is performed, but no postulated mechanism is proposed at present. This transformation shows incredible ­potential for widespread use in the synthesis of nitrogen-containing compounds in a complex ­setting.


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