39655-12-4Relevant articles and documents
Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation
M?ckel, Robert,Hille, Jessica,Winterling, Erik,Weidemüller, Stephan,Faber, Tabea Melanie,Hilt, Gerhard
supporting information, p. 442 - 445 (2018/02/21)
An electrochemical access to iodinated aromatic compounds starting from trimethylsilyl-substituted arenes is presented. By design of experiments, highly efficient and mild conditions were identified for a wide range of substrates. A functional group stability test and the synthesis of an important 3-iodobenzylguanidine radiotracer illustrate the scope of this process.
A practical transition metal-free aryl-aryl coupling method: Arynes as key intermediates
Leroux, Frederic R.,Bonnafoux, Laurence,Heiss, Christophe,Colobert, Francoise,Lanfranchi, Don Antoine
, p. 2705 - 2713 (2008/09/19)
Upon treatment of various aryllithium intermediates with 1,2-dibromobenzene or 1-bromo-2-iodobenzene, dissymmetrical ortho,ortho′-di-, tri-and even tetrasubstituted bromo- or iodobiaryls become readily available. The crucial steps in all these reactions were the nucleophilic addition of the organolithium precursor to a transient aryne species released from it by β-elimination of a lithium halide and, stabilization of the resulting 2-biaryllithium intermediate by in situ transfer of bromine or iodine from the starting material. This straightforward transition metal-free access to biaryls allows the preparation of highly valuable halobiaryls on a gram scale in excellent yields. These precursors can be subsequently functionalized by highly regioselective halogen/metal permutations into a vast variety of target molecules. This was demonstrated in the synthesis of several mono- and diphosphine ligands.
