Metalation of Aryl Iodides, Part II: Directed Ortho-Lithiation of 3-Iodo-N,N-diiospropyl-2-pyridinecarboxamide: Halogen-Dance and Synthesis of an Acyclic Analogue of Meridine

Publisher Website
Google Scholar
Abstract
For the second time, metalation of an iodopyridine was successfully achieved. Lithiation was ortho-directed by the iodo group which subsequently ortho-migrates to give a more stabilized iodolithiopyridine. An intermediate 4-lithio derivative could be trapped with chlorotrimethylsilane before iodo migration had occurred. The final 3-lithio compound was obtained in high yield which was reacted with electrophiles leading to various polysubstituted pyridines. The reaction was used for the preparation of an acyclic analogue of meridine, a new marine alkaloid.

This publication has 0 references indexed in Scilit: