A thiophene reagent in organic chemistry that especially promotes the Ullmann reaction between aryl halides.1 Used in direct N-arylation of imidazole and pyrazole with aryl iodides, aryl bromides, and aryl chlorides.2 Employed in palladium-catalyzed coupling of aryl and alkenyl iodides with boronic acids,3 palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids,4 palladium-catalyzed cross-coupling with boronic acids and organostannanes,5 cyclotrimerization of Oxabenzonorbornadiene,6 Ullmann-like reductive coupling of 1,4-diiodo-2,3,5,6-tetrafluorobenzene,7 synthesis of a series of bi(tetrathiafulvalenyl) derivatives from iodo-TTF precursors,8 and stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with Alkenyl, Aryl, and Heteroaryl Iodides.9 Also applied to promote modified Stille cross-coupling reactions.10
References:
1. Chem. Rev. 2002, 102, 1359.
2. Bull. Chem. Soc. Jpn. 2008, 81, 515.
3. Org. Lett. 2001, 3, 2149.
4. Org. Lett. 2001, 3, 91.
5. Synthesis 2005, 25.
6. Helv. Chim. Acta 2004, 87, 2364.
7. Tetrahedron 1998, 54, 14609.
8. J. Mater. Chem. 2000, 10, 1273.
9. J. Am. Chem. Soc. 2007, 129, 790.
10. Angew. Chem. Int. Ed. 2004, 43, 4704.