Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone
Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone
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DOI：
10.1021/acs.joc.8b02459
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发表时间：
2019-01-18
影响因子：
3.6
通讯作者：
Maurya, Ram Awatar
中科院分区：
文献类型：
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作者：
Borra, Satheesh;Chandrasekhar, D.;Maurya, Ram Awatar
以Ru（bpy）（3）（PF 6）（2）为光催化剂，在蓝光LED光照射下，将α-叠氮查尔酮与1/2-萘酚或2-羟基-1，4-萘醌偶联，以高产率（68-84%）得到2，3-稠合吡咯。整个转化过程包括α-叠氮查尔酮光敏分解为高反应活性的2 H-氮杂环丙烷，这些环丙烷被1/2-萘酚或2-羟基-1，4-萘醌捕获，导致两个新的C-N键和一个新的C-C键的构建。
alpha-Azidochalcones were coupled with 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone using Ru(bpy)(3)(PF6)(2) as a photocatalyst under blue LED light irradiation to yield 2,3-fused pyrroles in high yields (68-84%). The overall transformation involves photosensitized decomposition of alpha-azidochalcones into highly reactive 2H-azirines which are trapped by 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone, leading to the construction of two new C-N and one new C-C bonds.