过渡金属催化 2-氧代吲哚与苯并碘杂环戊二烯酮（EBX）试剂的无需过渡金属的氧化炔基化反应。
Transition-Metal Free Oxidative Alkynylation of 2-Oxindoles with Ethynylbenziodoxolone (EBX) Reagents.
机构信息
Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhopal, MP 462 066, India.
出版信息
J Org Chem. 2018 Jan 5;83(1):403-421. doi: 10.1021/acs.joc.7b02797. Epub 2017 Dec 26.
We report an efficient direct alkynylations of 3-alkyl/aryl 2-oxindoles employing ethynyl-1,2-benziodoxol-3(1H)-one (EBX) to afford a wide variety of 3-alkynyl-3-alkyl/aryl 2-oxindole under transition-metal free condition. In addition to activated carbonyl compounds viz. 2-oxindole-3-alkylcarboxylates, this direct alkynylations protocol works efficiently on 3-alkyl/aryl 2-oxindols as well thereby widening the scope even further. Eventually, a Pd(0)-catalyzed asymmetric decarboxylative allylation of few products is shown to furnish synthetically viable enantioenriched 2-oxindoles with C-3 quaternary stereocenters.
我们报告了一种高效的直接炔基化 3-烷基/芳基 2-氧吲哚的方法，使用乙炔基-1,2-苯并碘杂环酮（EBX）在无过渡金属条件下，可得到多种 3-炔基-3-烷基/芳基 2-氧吲哚。除了活性羰基化合物，如 2-氧吲哚-3-烷氧羰基化合物外，该直接炔基化反应还能有效地应用于 3-烷基/芳基 2-氧吲哚，从而进一步扩大了反应范围。最后，我们展示了一些产物的 Pd(0)催化不对称脱羧烯丙基化反应，以提供具有 C-3 季碳立体中心的合成上可行的对映体富集的 2-氧吲哚。
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