Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes
Date of Issue2015-06-08
School of Physical and Mathematical Sciences
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.
DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Angewandte chemie International edition
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