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TMSCH2Li-LiDMAE: a new nonnucleophilic reagent for C-2 lithiation of halopyridines |
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| Authors: | Abdelatif Doudouh Yves Fort |
| Institution: | a Synthèse Organométallique et Réactivité, UMR CNRS 7565, Université Henri Poincaré, Bd des Aiguillettes, 54506 Vandoeuvre-lès-Nancy, France b FMC Corporation, Lithium Division, Highway 161 Box 795, Bessemer City, NC 28016, USA |
| Abstract: | A new superbasic reagent has been discovered by combining TMSCH2Li and LiDMAE in hexane. This reagent was found highly efficient for the C-2 lithiation of sensitive chloro- and fluoropyridines. The metallation occurred chemo- and regioselectively at 0 °C avoiding the nucleophilic addition or substrate degradation commonly obtained with other alkyllithiums even at lower temperatures. |
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