Copper-catalyzed synthesis of medium- and large-sized nitrogen heterocycles via N-arylation of phosphoramidates and carbamates.

Org Lett

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.

Published: October 2005

[reaction: see text] We have developed an efficient method for the preparation of medium- and large-sized nitrogen heterocycles via copper-catalyzed intramolecular N-arylation of phosphoramidates and carbamates. Introduction of the phosphoryl group or tert-butoxycarbonyl at N-termini can improve intramolecular cyclization under copper catalysis, and the phosphoryl and tert-butoxycarbonyl can easily be removed under the mild conditions; thus, the convenient and efficient method is suitable for the preparation of medium- and large-sized nitrogen heterocycles.

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http://dx.doi.org/10.1021/ol052126cDOI Listing

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