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9.10.1.4.4.4.3 Variation 3: Palladium-Assisted Coupling Reactions

DOI: 10.1055/sos-SD-009-00363

Schatz, J.Science of Synthesis, (20019388.

Iodo- or bromothiophenes react with terminal alkenes[‌1087‌‌1089‌] or alkynes[‌1053‌,‌1090‌,‌1091‌] under catalysis by palladium(0) in a Heck-type coupling to give (alk-1-enyl)- or (alk-1-ynyl)thiophenes;[‌1090‌,‌1092‌‌1094‌] examples are given in Scheme 128. Sometimes, stoichiometric amounts of palladium(0) are necessary.[‌1088‌,‌1091‌,‌1095‌] In mixed bromoiodo-substituted thiophenes, the more reactive iodine atom is replaced selectively.[‌1096‌] Reaction without palladium catalysis but under photochemical conditions is possible, as shown by the synthesis of 1-nitro-5-(phenylethynyl)thiophene (87%) from 1-iodo-5-nitrothiophene and phenylacetylene.[‌771‌]

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