Journal of Organic Chemistry p. 2494 - 2498 (1990)
Update date:2022-08-02
Topics:
Deschamps, Eliane
Mathey, Francois
In the presence of AlCl3, the dienic system of a phosphole P-W(CO)5 complex can serve to alkylate electron-rich arenes such as anisole or heteroarenes such as furan and thiophene.The 2-aryl-2,5-dihydrophosphole complexes thus obtained can be converted into the corresponding 2-arylphospholes via decomplexation, reduction, bromination, and dehydrobromination.The overall yields are satisfactory.The thiophene ring can serve as a functionalizable carrier for the phosphole ring.Thus, a 2-(2-thienyl)phosphole P-W(CO)5 complex can be easily acetylated or formylated on the C5 position of the thiophene ring by CH3C(O)Cl + AlCl3 or HC(O)N(Me)Ph + POCl3, respectively.
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