871707-42-5Relevant articles and documents
Bromine-lithium exchange: An efficient tool in the modular construction of biaryl ligands
Bonnafoux, Laurence,Leroux, Frederic R.,Colobert, Francoise
, p. 1278 - 1287 (2011/10/31)
Regioselective bromine-lithium exchange reactions on polybrominated biaryls enable the modular synthesis of various polysubstituted biphenyls such as bis(dialkylphosphino)-, bis(diarylphosphino)- and dialkyl(diaryl) phosphinobiphenyls. All permutations of
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.
Ligand tailoring: The first modular assembly of atropisomeric biarylbisphosphine ligands
Leroux, Frédéric,Mettler, Hanspeter
, p. 766 - 770 (2007/10/03)
Strategies based on highly selective halogen-metal permutations have been devised and applied enabling the modular assembly of atropisomeric biaryl bisphosphines. After resolution on chiral column, the ligands were tested in benchmark hydrogenation reactions affording good to excellent enantioselectivity. Georg Thieme Verlag Stuttgart.