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- Title
Conversion of 2-Iodobiaryls into 2,2′-Diiodobiaryls via Oxidation-Iodination Sequences: A Versatile Route to Ladder-Type Heterofluorenes.
- Authors
Wu, Bin; Yoshikai, Naohiko
- Abstract
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.
- Subjects
POLYCYCLIC aromatic hydrocarbons; OXIDATION; IODINATION; RING-opening reactions; SALTS
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 30, p8860
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201503134