98751-25-8Relevant articles and documents
Arylation with 1,3-Dinitroarenes and Copper(I) t-Butoxide. Scope and Limitations
Carter, Stephen D.,Wallace, Timothy W.
, p. 1601 - 1633 (2007/10/02)
The reaction of 1,3-dinitrobenzene with copper(I) t-butoxide and an iodoarene, which produces a 2,6-dinitrobiphenyl, has been stidied in detail with a variety of substrates.Iodoarenes containing ester, aldehyde, or other halogen functions were effective, but replacement of the iodoarene with a bromoarene, iodoalkyne, or iodoalkene resulted in less efficient coupling, promoting side-reactions.On replacing the second nitro group on the dinitrobenezene with nitrile, ester, amide, or trifluoromethyl groups, little or no coupling was observed.Limiting side-reactions usually involved the decomposition of substrates by t-butoxide via nucleophilic substitution, elimination, or deprotonation.A mechanism based on reversible cupration of the dinitroarene is proposed.