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Volumn , Issue 1, 2009, Pages 47-50

Microwave-assisted aminocarbonylation of aryl bromides at low carbon monoxide pressure

Author keywords

Aminocarbonylation; Carbon monoxide; Microwave

Indexed keywords


EID: 62349096944     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087381     Document Type: Article
Times cited : (19)

References (44)
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    • Surprisingly the use of an additional ligand such as 1,1- bis(diphenylphosphino)ferrocene (dppf) had a negative influence on the reaction yields
    • Surprisingly the use of an additional ligand such as 1,1- bis(diphenylphosphino)ferrocene (dppf) had a negative influence on the reaction yields.
  • 30
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    • Working at 1 atm of CO at r.t., no reaction occurred after 24 h.
    • Working at 1 atm of CO at r.t., no reaction occurred after 24 h.
  • 31
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    • General Procedure for the Synthesis of Amides 8-14: A solution of the aryl bromide (0.46 mmol) and the amine (0.46 mmol) in anhyd THF (1.5 mL) was placed in a 10-mL tube for microwave reactions. DIPEA (240 μL, 1.38 mmol) and PdCl2 (PPh3)2 (16 mg, 0.023 mmol) were added and the solution was submitted to pressurized CO (120 psi) and inserted in the cavity of a Discover System (CEM Corporation).13,19 After heating for 20 min at 130°C at 150 W (value previously set on the microwave oven, the tube was cooled and the internal gas pressure was released. The reaction mixture was filtered, evaporated in vacuo and the amide was purified by flash chromatography. 4, 4-Fluorophenyl)carbonyl]morpholine (8, see ref. 30. 1, 4-Fluorophenyl)carbonyl]-4-phenylpiperazine (9, see ref. 31, S)-Methyl 2, 4-Fluorophenyl)formamido]-2-phenylacetate (10, 1H NMR (400 MHz, CDCl3, δ, 7.56 d
    • +.
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    • General Procedure for the Synthesis of Amides 18-24: A solution of 1 (0.35 mmol) and the amine (0.23 mmol) in anhyd THF (1 mL) was prepared in a 10-mL tube for microwave reactions. Anhyd Cs2CO3 (225 mg, 0.69 mmol) and PdCl2(PPh3)2 (16 mg, 0.023 mmol) were added and the solution was submitted to pressurized CO at 120 psi and heated for 30 min at 120°C by microwave at 200 W (as previously described for amides 8-14, The tube was cooled and the internal gas was released. The reaction mixture was filtered, evaporated in vacuo and the crude mixture was analysed by HPLC and/or purified by flash chromatography. 4-Ethyl-N-(3-nitrophenyl)benzamide (18, 1H NMR (400 MHz, CDCl3, δ, 8.45 (s, 1 H, 7.85-7.94 (m, 4 H, 7.32 (m, 1 H, 7.27 (d, J, 8.1 Hz, 2 H, 2.72 (q, J, 7.6 Hz, 2 H, 1.26 q, J, 7.6 Hz, 3 H, ES-MS: m/z, 271 [M, 1, 2
    • +.
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    • N-(5-Chloro-2-nitrophenyl)-4-ethylbenzamide (17, A solution of 1c (33 μL, 0.23 mmol) and 16 (40 mg, 0.23 mmol) in anhyd THF (1 mL) was prepared in a 10-mL tube for microwave reactions. Anhyd Cs2CO3 (225 mg, 0.69 mmol) and PdCl2 (PPh 3)2 (16 mg, 0.023 mmol) were added and the solution was submitted to pressurized CO at 120 psi and heated for 30 min at 120°C by microwave at 200 W (as previously described for amides 8-14, The tube was cooled and the internal gas was released. The reaction mixture was filtered, evaporated in vacuo and the crude mixture was analysed by HPLC and/or purified by flash chromatography. 1H NMR (400 MHz, CDCl3, δ, 11.51 (br s, 1 H, 9.13 (s, 1 H, 8.25 (d, J, 7.8 Hz, 1 H, 7.88 (d, J, 8.0 Hz, 2 H, 7.34 (d, J, 8.0 Hz, 2 H, 7.13 (d, J, 7.8 Hz, 1 H, 2.72 (q, J, 7.6 Hz, 2 H, 1.26 q, J, 7
    • 37Cl).
  • 42
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    • Eur. Patent Appl, EP 94-306464
    • Jacobson, R. M. Eur. Patent Appl., EP 94-306464, 2005.
    • (2005)
    • Jacobson, R.M.1
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    • Int. Patent Appl, WO 20040202
    • Jensen, J. L.; Burek, P. P. Int. Patent Appl., WO 20040202, 2004.
    • (2004)
    • Jensen, J.L.1    Burek, P.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.