Rhodium(III)-Catalyzed Oxidative Olefination of N-(Naphthalen-1-yl)amides

Xiaowei Wang; Xuting Li; Jian Xiao; Yi Jiang; Xingwei Li

doi:10.1055/s-0031-1290428

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(11): 1649-1652
DOI: 10.1055/s-0031-1290428

letter

Rhodium(III)-Catalyzed Oxidative Olefination of N-(Naphthalen-1-yl)amides

Xiaowei Wang

^aChengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, P. R. of China

^bDalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, P. R. of China

^cGraduate University of Chinese Academy of Sciences, The Chinese Academy of Sciences, Beijing 100049, P. R. of China, eMail: yjiang@cioc.ac.cn eMail: xwli@dicp.ac.cn

,

Xuting Li

^bDalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Jian Xiao

^bDalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Yi Jiang*

^aChengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, P. R. of China

,

Xingwei Li*

^bDalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, P. R. of China

› Institutsangaben

Abstract

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Abstract

Rhodium(III)-catalyzed oxidative coupling of N-(naphthalen-1-yl)amides with acrylates and styrene was achieved through selective C–H bond activation at the peri position. This reaction proceeded smoothly to give the direct olefination product or the corresponding olefination–cyclization product. High functional-group tolerance was observed

Keywords

oxidative olefination - C–H activation - rhodium

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Referenzen

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13 Typical Procedure of Olefination Reactions A pressure tube was charged with Ag₂CO₃ (297 mg, 1.08 mmol, 2 equiv), [RhCp^*Cl₂]₂ (13.3 mg, 0.0216 mmol, 4 mol%), and 1a (100 mg, 0.54 mmol, 1 equiv). After purging with nitrogen, MeCN (3 mL) and 2c (138 mg, 1.08 mmol, 2 equiv) were added. The tube was sealed, and the mixture was stirred at 115 °C for 16 h, followed by diluting with CH₂Cl₂ and filtration through Celite. All volatiles were removed under reduced pressure. The purification was performed by flash column chromatography on silica gel using EtOAc in PE to give 3c (yield 89%). Spectral Data Compound 3c (major isomer): ¹H NMR (500 MHz, CDCl₃): δ = 7.66 (d, J = 8.2 Hz, 1 H), 7.58–7.47 (m, 1 H), 7.42 (s, 2 H), 7.39–7.32 (m, 1 H), 6.97 (s, 1 H), 6.03 (s, 1 H), 3.25 (d, J = 14.8 Hz, 1 H), 2.99–2.85 (m, 1 H), 2.54 (s, 3 H), 1.19 (s, 9 H). ¹³C NMR (126 MHz, CDCl₃): δ = 169.48, 168.64, 141.86, 138.77, 131.64, 129.96, 128.59, 128.32, 123.53, 119.07, 117.65, 107.05, 80.63, 62.67, 40.33, 27.75, 25.41. ESI-HRMS: m/z calcd for [C₁₉H₂₁NO₃ + H]⁺: 312.1599; found: 312.1592. Compound 5a: ¹H NMR (500 MHz, DMSO): δ = 9.90 (s, 1 H), 8.10 (d, J = 16.0 Hz, 1 H), 7.95–7.84 (m, 2 H), 7.62 (d, J = 7.4 Hz, 2 H), 7.55–7.46 (m, 3 H), 7.40 (t, J = 7.7 Hz, 2 H), 7.33 (d, J = 7.2 Hz, 1 H), 7.27 (t, J = 7.3 Hz, 1 H), 6.75 (d, J = 16.0 Hz, 1 H), 1.82 (s, 3 H). ¹³C NMR (126 MHz, DMSO): δ = 169.37, 137.95, 135.82, 135.47, 134.54, 130.87, 129.35, 129.27, 129.16, 129.05, 128.24, 128.01, 127.91, 127.65, 126.83, 126.12, 126.04, 23.49. ESI-HRMS: m/z calcd for [C₂₀H₁₇NO + H]⁺: 288.1388; found: 288.1394. Compound 6a: ¹H NMR (500 MHz, CDCl₃): δ = 8.01 (d, J = 7.1 Hz, 1 H), 7.68 (d, J = 8.2 Hz, 1 H), 7.53–7.43 (m, 3 H), 7.40–7.16 (m, 6 H), 6.81 (d, J = 15.8 Hz, 1 H), 6.22 (dd, J = 15.8, 8.3 Hz, 1 H), 6.06 (d, J = 8.2 Hz, 1 H), 2.40 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 169.68, 142.73, 138.26, 135.72, 132.02, 131.33, 129.60, 129.08, 128.78, 128.44, 128.09, 127.18, 126.71, 123.96, 119.33, 117.29, 110.84, 69.33, 24.43. ESI-HRMS: m/z calcd for [C₂₁H₁₇NO + H]⁺: 300.1388; found: 300.1382. Compound 3gg: ¹H NMR (500 MHz, CDCl₃): δ = 7.52 (d, J = 8.4 Hz, 1 H), 7.43–7.38 (m, 1 H), 7.29–7.24 (m, 1 H), 7.11 (dd, J = 6.9, 1.4 Hz, 1 H), 6.95 (d, J = 8.2 Hz, 1 H), 6.24 (d, J = 7.2 Hz, 1 H), 5.07 (m, 1 H), 3.72–3.59 (m, 2 H), 3.49–3.38 (m, 1 H), 3.33 (dd, 1 H), 2.38–2.29 (m, 1 H), 2.27–2.18 (m, 1 H), 1.72–1.67 (m, 2 H), 0.98 (t, J = 7.4 Hz, 3 H). ¹³C NMR (126 MHz, CDCl₃): δ = 151.86, 141.90, 132.01, 130.29, 129.90, 127.85, 122.84, 115.80, 112.05, 97.57, 65.99, 59.05, 48.06, 35.33, 20.90, 11.74. ESI-HRMS: m/z calcd for [C₁₆H₁₉NO + H]⁺: 242.1545; found: 242.1549
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