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Synfacts 2015; 11(1): 0078
DOI: 10.1055/s-0034-1379648
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Mediated Synthesis of Pyrroles

Contributor(s):
Paul Knochel
,
Diana Haas
Yu S, Xiong M, Xie X, Liu Y * Shanghai Institute of Organic Chemistry, P. R. of China
Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis of N–H and N-Substituted Pyrroles.

Angew. Chem. Int. Ed. 2014;
53: 11596-11599
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

zirconium - nitriles - cyclization

Significance

Liu and co-workers report the direct insertion of nitriles into zirconocene-1-aza-1,3-diene complexes for the synthesis of variously substituted N–H and N-substituted pyrroles in high yields.


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Comment

The outcome of the reaction is determined by different cyclization patterns that depend on the relative stability and reactivity of the enamine–imine tautomers that are formed upon hydrolysis of the diazazirconacycles.


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