1833-43-8Relevant academic research and scientific papers
Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine-Directed para and ortho C?H Functionalization
Wu, Yichen,Bouvet, Sébastien,Izquierdo, Susana,Shafir, Alexandr
, p. 2617 - 2621 (2019)
Among halogenated aromatics, iodoarenes are unique in their ability to produce the bench-stable halogen(III) form. Earlier, such iodine(III) centers were shown to enable C?H functionalization ortho to iodine via halogen-centered rearrangement. The broader implications of this phenomenon are explored by testing the extent of an unusual iodane-directed para C?H benzylation, as well as by developing an efficient C?H coupling with sulfonyl-substituted allylic silanes. Through the combination of the one-shot nature of the coupling event and the iodine retention, multisubstituted arenes can be prepared by sequentially engaging up to three aromatic C?H sites. This type of iodine-based iterative synthesis will serve as a tool for the formation of value-added aromatic cores.
