Direct sp3C–H bond activation adjacent to nitrogen in heterocycles
Top Cited Papers
- 1 March 2007
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 36 (7), 1069-1084
- https://doi.org/10.1039/b607547a
Abstract
Activation of sp3 C–H bonds adjacent to nitrogen in heterocycles is an attractive transformation that is emerging as a practical method in organic synthesis. This tutorial review aims to summarize the key examples of direct functionalization of nitrogen-containing heterocycles via metal-mediated and metal-catalyzed processes, which is meant to serve as a foundation for future investigations into this rapidly developing area of research. The review covers functionalization of N-heterocycles via α-lithiation with alkyllithium/diamine complexes, α-amino radical formation, metal-catalyzed direct C–H activation, C–H oxidations and oxidative couplings, and metal-catalyzed carbene insertions.Keywords
This publication has 58 references indexed in Scilit:
- Selective benzylic lithiation of N-Boc-2-phenylpiperidine and pyrrolidine: expedient synthesis of a 2,2-disubstituted piperidine NK1 antagonistTetrahedron Letters, 2005
- Boron trifluoride etherate-assisted ring opening of ethylene oxide by a chiral organolithium: enantioselective synthesis of (R)-N-Boc-2-(2-hydroxyethyl)pyrrolidineTetrahedron: Asymmetry, 2005
- Synthesis of Chiral 1,2-Diamines by Asymmetric Lithiation−SubstitutionOrganic Letters, 2001
- The diastereoselective and enantioselective substitution reactions of an isoindoline–borane complexJournal of the Chemical Society, Perkin Transactions 1, 1999
- Formation and reaction of 2-metalated N-Boc-4,4-dimethyl-1,3-oxazolidines in the presence of (−)-sparteine: new chiral formyl anion equivalentsTetrahedron: Asymmetry, 1998
- Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/(−)-SparteineThe Journal of Organic Chemistry, 1997
- Regioselective, Diastereoselective, and Enantioselective Lithiation−Substitution Sequences: Reaction Pathways and Synthetic ApplicationsAccounts of Chemical Research, 1996
- Complex Induced Proximity Effects: Enantioselective Syntheses Based on Asymmetric Deprotonations of N-Boc-pyrrolidinesJournal of the American Chemical Society, 1994
- .alpha.-Lithioamine synthetic equivalents: syntheses of diastereoisomers from Boc derivatives of cyclic aminesThe Journal of Organic Chemistry, 1993
- α-Lithioamine synthetic equivalents from dipole-stabilized carbanions: The t-Boc group as an activator for α′-lithiation of carbamatesTetrahedron Letters, 1989