New methods for the synthesis of proximally functionalized aryl Boranes and silanes.

The synthesis of ten novel disubstituted aromatic compounds is reported. New methods that were developed for the synthesis include (1) single l-Li exchange of 1,8-diiodonaphthalene, (2) use of Me(3)SiOSO(2)CF(3) to form C-Si bonds in sterically hindered situations, and (3) protection of an organoborane as an ethoxy ate complex during halogen-metal exchange and substitution on the organic residue. In addition, the dimethylborylation of arylithium reagents with Me(2)BOEt was generalized to include labile nucleophiles. The methods are geared to the synthesis of peri-substituted napthalenes as anion receptors, but should be of more general utility as well. Finally, some special properties of the newly synthesized compounds are discussed.