Subscribe to RSS
Click and Homocoupling for Extended π-Systems
M. Juríček, K. Stout, P. H. J. Kouwer, A. E. Rowan*
Radboud University Nijmegen, The Netherlands
19 August 2011 (online)
Extending its π-system is a convenient way of red-shifting the absorption maximum of a dye molecule. Starting from ortho-bis(haloacetylene) derivatives 1 and 4, the authors use a copper-catalyzed azide-haloalkyne cycloaddition reaction (CuAHAC) and a subsequent homocoupling reaction to add a benzene and two triazole units to an aromatic system. Depending on the utilized azide, they obtain between 14% and 66% total yield over both steps starting from 1.