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Conversion of 2‐Iodobiaryls into 2,2′‐Diiodobiaryls via Oxidation‐Iodination Sequences: A Versatile Route to Ladder‐Type Heterofluorenes
Author(s) -
Wu Bin,
Yoshikai Naohiko
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503134
Subject(s) - conjugated system , ring (chemistry) , combinatorial chemistry , catalysis , chemistry , halogenation , type (biology) , stereochemistry , nanotechnology , organic chemistry , materials science , polymer , biology , ecology
Even though 2,2′‐diiodo‐ and 2,2′‐dibromobiaryls represent accomplished precursors for heterofluorenes and other extended π‐conjugated systems, their preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report a convenient method for the preparation of various 2,2′‐diiodobiaryls from 2‐iodobiaryls via cyclic diaryliodonium intermediates. An iodinative ring‐opening of the diaryliodonium salts, mediated by a copper/diamine catalyst system, is able to afford the corresponding 2,2′‐diiodobiaryls under mild conditions. The versatility of this two‐step approach is demonstrated by the preparation of hitherto unexplored tetraiodoteraryls and their conversion into ladder‐type π‐conjugated systems.