锌-金协同催化苯并呋喃的直接炔基化反应。

Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH4306, 1015 Lausanne, Switzerland.

Beilstein J Org Chem. 2013 Aug 29;9:1763-7. doi: 10.3762/bjoc.9.204. eCollection 2013.

The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP).

首次使用高价碘试剂 1-[(三异丙基硅基)乙炔基]-1,2-苯并碘杂环戊烯-3(1H)-酮（TIPS-EBX），通过金催化剂和锌路易斯酸的协同作用，实现了苯并呋喃的直接炔基化。带有烷基、芳基、卤素和醚基团取代基的苯并呋喃的 C2-炔基化反应具有很高的选择性。该反应在更复杂的药物 8-甲氧基补骨脂素（8-MOP）的情况下也取得了成功。