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10.1.1.2.3.3.1 6π-Electrocyclization/Dehydrogenation of 2,3-Di(alkenyl)furans

DOI: 10.1055/sos-SD-110-00529

Kwiecień, H.Science of Synthesis Knowledge Updates, (20144225.

2,3-Dibromofurans 444 react with acrylates or styrenes under Heck reaction conditions to afford 2,3-di(alkenyl)furans 445, which can be transformed into functionalized ben­zo[b]furans 446 by a domino 6π-electrocyclization/dehydrogenation sequence (Scheme 192).[‌347‌] The electrocyclization of 2,3-di(alkenyl)furans requires drastic reaction conditions, e.g. a temperature of 200 °C and a long reaction time. The transformation of 2,3-di(alkenyl)furans having an ethoxycarbonyl group on the furan ring at the 5-position require less drastic conditions (stirring at 170 °C, 2 × 12 h).

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