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Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine‐Directed para and ortho C−H Functionalization

AuthorsWu, Yichen; Bouvet, Sébastien; Izquierdo, Susana ; Shafir, Alexandr
KeywordsC−C coupling
C−H functionalization
Hypervalent iodine
Iterative methods
Oxidative coupling
Issue Date25-Feb-2019
CitationAngewandte Chemie - International Edition 58 (9): 2617-2621 (2019)
AbstractAmong 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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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