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Synthesis 1997; 1997(9): 1027-1033
DOI: 10.1055/s-1997-1310
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Rhodium(I)-Mediated Synthesis of Benzo[2,1-b:3,4-b':5,6-c'']trithiophenes and Naphtho[2,1-b:3,4-b']dithiophenes

Uwe Dahlmann
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Publication Date:
31 December 2000 (online)

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The syntheses of carbonylated benzo[2,1-b:3,4-b':5,6-c'']trithiophenes 2 and naphtho[2,1-b:3,4-b']dithiophenes 3 are described. The treatment of 5,5'-dicarbonylated 3,3'-bis(phenylethynyl)-2,2'-bithiophenes 6 [readily available via Pd(II)-catalyzed alkynylation of the corresponding 3,3'-dibromo-2,2'-bithiophenes 5 in the presence of Cu(I) in (i-Pr)2NH] with chlorotris(triphenylphosphine)rhodium(I) yields the cyclic rhodium complexes 7 which smoothly react with sulfur and acetylenes to give 2 and 3 in good yields.

rhodium(I)