Reddy Singam Maneesh Kumar, Suri Babu Undamatla, Suresh Vavilapalli, Nanubolu Jagadeesh Babu, Sridhar Reddy Maddi
Department of Organic Syntheis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Academy of Scientific and Innovative Research, Ghaziabad 201002, India.
Org Lett. 2021 Oct 15;23(20):7888-7893. doi: 10.1021/acs.orglett.1c02890. Epub 2021 Oct 6.
Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (/) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.
鉴于异香豆素类似物在天然产物和药物中无处不在，它们是合成化学家最青睐的骨架之一。本文公开了一种利用苯甲酰铵盐（酰铵作为无痕导向基团）与炔丙醇进行环化反应的双（/）C-H和C-C活化反应，通过铑催化，从易得的起始原料快速合成新型异香豆素。该操作简单的方案具有广泛的底物范围和良好的官能团耐受性。重要的是，该方案无需任何化学计量的金属氧化剂，且在有氧条件下进行。
