2024-03-28T13:18:12Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/2022372020-10-20T06:58:34Zcom_10261_5063com_10261_5col_10261_5066
Wu, Yichen
Bouvet, Sébastien
Izquierdo, Susana
Shafir, Alexandr
2020-02-28T08:45:37Z
2020-02-28T08:45:37Z
2019-02-25
Angewandte Chemie - International Edition 58 (9): 2617-2621 (2019)
http://hdl.handle.net/10261/202237
10.1002/anie.201809657
http://dx.doi.org/10.13039/501100003329
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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
eng
openAccess
C−C coupling
C−H functionalization
Hypervalent iodine
Iterative methods
Oxidative coupling
Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine‐Directed para and ortho C−H Functionalization
artículo