Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic Intermediates
- 4 April 2011
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (9), 2306-2309
- https://doi.org/10.1021/ol200563j
Abstract
Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF(3)·OEt(2). A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of TMP bases in the presence or absence of BF(3)·OEt(2).Keywords
This publication has 43 references indexed in Scilit:
- Direct Cross‐Coupling of C-H Bonds with Grignard Reagents through Cobalt CatalysisAngewandte Chemie, 2010
- Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic AcidsJournal of the American Chemical Society, 2010
- Palladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsChemical Reviews, 2010
- Organotrifluoroborates and Monocoordinated Palladium Complexes as Catalysts—A Perfect Combination for Suzuki–Miyaura CouplingAngewandte Chemie, 2009
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie, 2009
- Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse ArchitecturesAngewandte Chemie, 2007
- TMSCH2Li-induced regioselective lithiation of (S)-nicotineOrganic & Biomolecular Chemistry, 2006
- The Quest for Quinine: Those Who Won the Battles and Those Who Won the WarAngewandte Chemie, 2005
- The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive FunctionalizationAngewandte Chemie, 2004
- Neuartige, durch Azokupplung von Chinaalkaloiden hergestellte chirale Phasen zur EnantiomerentrennungArchiv der Pharmazie, 1989