卡宾催化吲哚 3-位 C(sp3)-H 键功能化反应
Carbene-Catalyzed Indole 3-Methyl C(sp)-H Bond Functionalization.
机构信息
Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
出版信息
J Org Chem. 2017 Dec 15;82(24):13342-13347. doi: 10.1021/acs.joc.7b02436. Epub 2017 Nov 22.
The metal-free catalytic functionalization of aromatic sp-carbons and benzylic sp-carbons remains challenging. Here we report a carbene-catalyzed functionalization of the 3-methyl sp-carbon attached to 2-formyl-indoles. The reaction proceeds through an NHC-bound o-quinodimethane as the key intermediate generated from 2-formyl-3-methylindoles under oxidative conditions. Reactive ketones are found to be effective substrates to produce substituted hydropyrano[3,4-b]indoles in good to excellent yields.
无金属催化的芳族 sp 碳和苄基 sp 碳的功能化仍然具有挑战性。在这里，我们报告了一种卡宾催化的 2-甲酰吲哚连接的 3-甲基 sp 碳的功能化。该反应通过 NHC 结合的 o-醌二甲基甲烷作为关键中间体进行，该中间体是在氧化条件下由 2-甲酰-3-甲基吲哚生成的。反应性酮被发现是有效的底物，可以高产率得到取代的氢吡喃并[3,4-b]吲哚。
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