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Palladium‐Catalyzed C−H Iodination of Arenes by Means of Sulfinyl Directing Groups
Author(s) -
Saito Hayate,
Yamamoto Keita,
Sumiya Yosuke,
Liu LingJun,
Nogi Keisuke,
Maeda Satoshi,
Yorimitsu Hideki
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000591
Subject(s) - halogenation , palladium , chemistry , catalysis , aryl , sulfur , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
C−H iodination of aromatic compounds has been accomplished with the aid of sulfinyl directing groups under palladium catalysis. The reaction proceeds selectively at the peri ‐position of polycyclic aryl sulfoxides or at the ortho ‐position of phenyl sulfoxides. The iodination products can be further converted via iterative catalytic cross‐coupling at the expense of the C−I and C−S bonds. Computational studies suggest that peri ‐C−H palladation would proceed via a non‐directed pathway, wherein neither of the sulfur nor oxygen atom of the sulfinyl group coordinates to the palladium before and at the transition state.