Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy District, 502284 Hyderabad, Telangana, India.
J Org Chem. 2022 Aug 5;87(15):10158-10172. doi: 10.1021/acs.joc.2c01101. Epub 2022 Jul 14.
Herein, we present an efficient and straightforward strategy enabling access to 2,3-disubstituted benzo[]furans. The whole synthetic process proceeds a domino intermolecular Sonogashira coupling of 2-(2-bromophenoxy)-1-phenylethan-1-ones/alkyl 2-(2-bromophenoxy)acetates/2-(2-bromophenoxy)acetonitrile/1-(2-bromophenoxy)propan-2-one with terminal acetylenes followed by an intramolecular carbanion-yne cyclization in a 5-- manner and subsequent double-bond isomerization. Notably, two C-C bonds have been constructed in a one-pot manner and a wide variety of (3-benzylbenzofuran-2-yl)(phenyl)methanones were accomplished with good functional group tolerance.
在此，我们提出了一种高效、直接的策略，可用于合成 2,3-二取代苯并呋喃。整个合成过程包括 2-(2-溴苯氧基)-1-苯乙酮/烷基 2-(2-溴苯氧基)乙酸酯/2-(2-溴苯氧基)乙腈/1-(2-溴苯氧基)丙-2-酮/末端炔烃的分子间多米诺 Sonogashira 偶联，随后在 5-位进行分子内碳负离子-炔烃环化反应和随后的双键异构化。值得注意的是，两个 C-C 键以一锅法的方式构建，并且多种（3-苄基苯并呋喃-2-基）（苯基）甲酮可以在良好的官能团容忍度下完成。
