Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• vinblastine (58a) and vincristine (58b) contain such a system. Aryl C-C bond formation As a final extension of this methodology, we probed the feasibility of this methodology in aryl-aryl C-C bond formation reactions. Accordingly, the diazonium salt 62 was prepared from indoline (59), and treated with one

• could also undergo direct formation of the radical 69. Rearomatization from 69 might then occur through a number of pathways; in one of these, the radical intermediate 69 would lose a proton to yield the radical anion 70 which, upon oxidation by loss of single electron to the starting diazonium salt 62