Preparation of a New Spirobi[thieno[2,3-c]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives

Abstract

3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.

Key words

lithiation - Negishi cross coupling - oligothiophene - organozinc reagent - spiro compound

• References

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