An easy one-pot desilylation/copper-free Sonogashira cross-coupling reaction assisted by tetra-butylammonium fluoride (TBAF): synthesis of highly π-conjugated porphyrins

Sonogashira cross-coupling is a key reaction for the synthesis of highly conjugated oligomers. However, its application has well known drawbacks; it requires drastic inert atmosphere conditions, generates homocoupling by-product of the terminal alkyne and others. In this paper, we describe a new and easy procedure using PdCl2(PPh3)2 as catalyst assisted by TBAF in a one-pot desilylation/copper-free Sonogashira reaction for the synthesis of highly conjugated porphyrin oligomers.

Graphical abstractDownload full-size image