C–H allylation of N-aryl-tetrahydroisoquinolines by merging photoredox catalysis with iodide catalysis

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• 作者：Zhujia Feng ; Tingting Zeng ; Jun Xuan ; Yunhang Liu ; Liangqiu Lu…
• 关键词：visible light photocatalysis ; iodide catalysis ; allylation ; tetrahydroisoquinolines
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：59
• 期：2
• 页码：171-174
• 全文大小：689 KB
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  10.For detailed condition optimization, including the evaluation of photocatalysts, solvents, light sources and bases, see Supporting Information
  11.General Procedure: In a 10 mL dry flask equipped with magnetic bar was charged with 1 (0.5 mmol, 1.0 equiv.) and Ir(bpy)2(dtbbpy)PF6 (2 mol%), 5 (0.75 mmol, 1.5 equiv.), KI (20 mol%), NaCO2CF3 (1.0 mmol, 2.0 equiv.) and MeCN (5 mL). The mixture was degassed via freeze-pump-thaw method (3 times) and then stirred under the irradiation of 7 W blue LEDs at room temperature for 12 h. The resultant mixture was filtered under vacuum to remove the solid. The filtrate was purified by flash chromatography on silica gel (petroleum ether/DCM=10:1) to afford the desired product 3. Analytical data of 1-allyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline (3a): light yellow oil; 1H NMR (600 MHz, CDCl3) δ (ppm) 7.18 (m, 6H), 6.89 (d, J=8.2 Hz, 2H), 6.73 (t, J=7.1 Hz, 1H), 5.89–5.82 (m, 1H), 5.06 (t, J=13.1 Hz, 2H), 4.74 (t, J=6.7 Hz, 1H), 3.72–3.52 (m, 2H), 3.08–2.96 (m, 1H), 2.88 (dt, J=15.7, 5.2 Hz, 1H), 2.78–2.65 (m, 1H), 2.49 (dt, J=14.1, 7.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ (ppm) 149.4, 138.1, 135.6, 134.9, 129.2, 128.5, 127.3, 126.5, 125.7, 117.2, 117.0, 113.8, 59.3, 41.9, 40.9, 27.4; HRMS: m/z (ESI) calculated [M+H]+ 250.1590, measured 250.1594.
  
• 作者单位：Zhujia Feng (1)
  Tingting Zeng (1)
  Jun Xuan (1)
  Yunhang Liu (1)
  Liangqiu Lu (1)
  Wen-Jing Xiao (1)
  
  1. CCNU-uOttawa Joint Research Center, College of Chemistry, Central China Normal University, Wuhan, 430079, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chinese Library of Science
  Chemistry
  
• 出版者：Science China Press, co-published with Springer
• ISSN：1869-1870

文摘

A dual catalytic system, combing visible light photoredox catalysis and iodide catalysis, has been developed for the functionalization of inert C–H bonds. By doing so, radical allylation reactions of N-aryl-tetrahydroisoquinolines (THIQs) were realized under extremely mild conditions, affording a wide variety of allyl-substituted THIQs in up to 78% yields. Keywords visible light photocatalysis iodide catalysis allylation tetrahydroisoquinolines