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14.3.1.4.3.2 Method 2: Alkenyl and Aryl Coupling Reactions

DOI: 10.1055/sos-SD-014-00183

Afarinkia, K.; Vinader, V.Science of Synthesis, (200314309.

Displacement of a halogen group for an alkenyl or aryl group is a particularly attractive method for the preparation of 2H-pyran-2-ones for two reasons. Firstly, it allows a diverse range of analogues to be prepared from a single molecule, making parallel synthesis viable and efficient. Secondly, it allows access to a number of 2H-pyran-2-ones that would be difficult to make otherwise. For instance, 2H-pyran-2-ones bearing only a 5-alkenyl or 5-aryl substituent are difficult to make by cyclization routes, whereas they are easily made by coupling reactions. Both Suzuki (Scheme 65 and Table 7) and Stille (Scheme 66) couplings have been reported, as well as some palladium-catalyzed displacements.[‌6‌,‌222‌,‌228‌‌231‌]

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