N,N,N′,N′,N”-Pentamethyldipropylenetriamine (PMDPTA): A Versatile Auxiliary for Site Selective Lithiation Reactions

Abstract Efficient lithiation processes were developed with PMDPTA, a tridentate ligand of butyllithium reagent for site selective metallation of aromatic and heteroaromatic compounds.

[1]  F. Faigl,et al.  Competition and co-operation between directing groups and activating agents: Regioselective metallation of 1-(methoxyphenyl)pyrroles , 1997 .

[2]  László Hegedu˝s,et al.  Hydrogenation of pyrrole derivatives I. Hydrogenations over palladium , 1996 .

[3]  M. Schlosser Organometallics in synthesis : a manual , 1994 .

[4]  P. Grimes,et al.  A predicative model for certain directed metalations, II; application to the behavior of p-fluoroanisole , 1994 .

[5]  S. Arai,et al.  The Effects of Tertiary Amine Catalysts on Moldability in High Resiliency Foam , 1988 .

[6]  H. Gross Über α‐Halogenäther, XII1) Darstellung von N‐substituierten Pyrrolen aus 2.5‐Dichlor‐tetrahydrofuran2) , 1962 .

[7]  L. C. Gibbons,et al.  The Synthesis and Purification of Ethers , 1947 .

[8]  Geoffrey Wilkinson,et al.  Comprehensive Organometallic Chemistry II , 1995 .

[9]  M. Schlosser,et al.  N-phenylpyrrole: A kinetic, though not thermodynamic preference for dilithiation , 1993 .

[10]  M. Schlosser,et al.  The metalation of fluoroanisoles: optional regioselectivity due to metal mediated control , 1991 .

[11]  M. Schlosser,et al.  Superbase Reactions: The Expedient and Selective Metalation of Fluorine- or Trifluoromethyl-Substituted Benzenes , 1990 .

[12]  J. M. Brittain,et al.  Pyrrole Studies XXVII.1 Utilisation of 1-Methyl-2-pyrrolyl Lithium in the Synthesis of 1-Methyl-2-substituted Pyrroles , 1982 .

[13]  D. Chadwick,et al.  Reaction between N-alkylpyrroles and alkyl-lithium reagents. The role of nitrogen substituent, solvent, alkyl-lithium, and complexing agents , 1979 .