Cobalt(II)-catalyzed intramolecular C-H amination with phosphoryl azides: formation of 6- and 7-membered cyclophosphoramidates

Hongjian Lu; Jingran Tao; Jess E Jones; Lukasz Wojtas; X Peter Zhang

doi:10.1021/ol100110z

Cobalt(II)-catalyzed intramolecular C-H amination with phosphoryl azides: formation of 6- and 7-membered cyclophosphoramidates

Org Lett. 2010 Mar 19;12(6):1248-51. doi: 10.1021/ol100110z.

Authors

Hongjian Lu¹, Jingran Tao, Jess E Jones, Lukasz Wojtas, X Peter Zhang

Affiliation

¹ Department of Chemistry, University of South Florida, Tampa, Florida 33620-5250, USA.

PMID: 20184343
DOI: 10.1021/ol100110z

Abstract

A highly effective Co(II)-based system has been developed for catalytic intramolecular C-H amination with phosphoryl azides without the need of terminal oxidant or other additives, resulting in the high-yielding production of cyclophosphoramidates with nitrogen gas as the byproduct. Additional features of this new catalytic system include the amination of primary C-H bonds and formation of 7-membered-ring structures.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Amination
Azides / chemistry*
Catalysis
Cobalt / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Organophosphorus Compounds / chemistry*
Phosphoric Acids / chemical synthesis*
Phosphoric Acids / chemistry
Stereoisomerism

Substances

Amides
Azides
Organometallic Compounds
Organophosphorus Compounds
Phosphoric Acids
Cobalt
phosphoramidic acid