A new method for the synthesis of dinaphtho[1,2-b;2′,1′-d]thiophenes and selenophenes

Naphthalene-1-sulfonic acid dimethylamides were treated with n-BuLi and elemental sulfur or selenium to afford dinaphtho[1,2-b:2',1'-d]thiophenes and selenophenes, respectively. This is the first example of making two C-S/Se bonds and a C-C bond in a single step at room temperature and also demonstrates a useful method for the synthesis of both thiophenes and selenophenes on naphthalene. in the case of the reactions of elemental selenium, diselenides were also obtained along with dinaphtho[1,2-b:2',1'-d]selenophenes. The structure of dinaphtho[1,2-b:2',]'-d]thiophene was characterized by X-ray crystallography as a representative molecule. (c) 2007 Wiley Periodicals, Inc.