Synfacts 2011(9): 0958-0958  
DOI: 10.1055/s-0030-1261023
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Click and Homocoupling for Extended π-Systems

Contributor(s): Timothy M. Swager, Jan M. Schnorr
M. Juríček, K. Stout, P. H. J. Kouwer, A. E. Rowan*
Radboud University Nijmegen, The Netherlands
Further Information

Publication History

Publication Date:
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.