Institute of Next Generation Matter Transformation, College of Chemical Engineering, College of Material Sciences Engineering at Huaqiao University , 668 Jimei Boulevard, Xiamen, Fujian 361021, P. R. China.
Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
Org Lett. 2016 Aug 19;18(16):4088-91. doi: 10.1021/acs.orglett.6b01934. Epub 2016 Aug 8.
A mild, transition metal-free, diborane-mediated deoxygenation of nitro groups was discovered that in situ generates nitrosoarene reactive intermediates. This new reactivity mode of B2pin2 was leveraged to construct indoles from o-nitrostyrenes through a reductive-cyclization reaction that exhibits a Hammett ρ-value of +0.97 relative to σpara values. Our new deoxygenation reaction is efficient, practical, and scaleable, enabling access to a broad range of indoles.
我们发现了一种温和、无过渡金属、硼烷介导的硝基脱氧反应，该反应能原位生成亚硝芳烃反应中间体。这种 B2pin2 的新反应模式可用于通过还原环化反应从邻硝基苯乙烯构建吲哚，该反应的哈米特 ρ 值相对于 σpara 值为+0.97。我们的新脱氧反应高效、实用且可规模化，可广泛应用于吲哚的合成。
