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Synlett 2016; 27(20): 2826-2830
DOI: 10.1055/s-0036-1588316
DOI: 10.1055/s-0036-1588316
letter
One-Pot Synthesis of Carbamoyl Azides via Palladium-Catalysed Azidocarbonylation of Haloarenes Using N-Formylsaccharin as a CO Surrogate
Authors
Weitere Informationen
Publikationsverlauf
Received: 06. August 2016
Accepted after revision: 27. August 2016
Publikationsdatum:
19. September 2016 (online)
Abstract
A highly efficient one-pot synthesis of carbamoyl azides from haloarenes and sodium azide has been developed. The protocol involves palladium-catalysed azidocarbonylation of haloarenes utilizing N-formylsaccharin as a CO source to form acyl azides, which undergo in situ Curtius rearrangement to afford the desired carbamoyl azides. N-Formylsaccharin is an easy-to-handle solid alternative to CO gas.
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- 21 General Procedure for the One-Pot Synthesis of Carbamoyl Azides 3: A mixture of haloarene 1 (1 mmol), sodium azide (3 mmol), Na2CO3 (2.5 mmol), Pd(OAc)2 (2 mol%), xantphos (5 mol%), N-formylsaccharin (2, 2.5 mmol), and DMF (3 mL) was stirred at 80 °C for 12–14 h under a nitrogen atmosphere (Scheme 3). After confirming the complete conversion of aldehyde into the corresponding carbamoyl azide (TLC), H2O (5 mL) was added and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phase was dried over anhyd Na2SO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane–EtOAc (4:1) as eluent to afford an analytically pure sample of product 3. All the compounds 3 are known and were characterized by comparison of their spectroscopic data with those reported in the literature (see refs. 15a, 18a and 21). Characterization data of selected compounds 3 are given below: Compound 3a (refs 18a and 15b): white solid; mp 84–86 °C (ref. 15b: 86–87 °C). 1H NMR (400 MHz, CDCl3): δ = 7.47 (d, J = 7.9 Hz, 2 H), 7.32–7.36 (m, 2 H), 7.10 (t, J = 7.3 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 154.08, 136.76, 129.25, 124.54, 119.38. HRMS (EI): m/z calcd for C7H6N4O: 162.0542; found: 162.0544. Compound 3c (refs 18a and 22): colourless solid; mp 103–104 °C (ref. 6: 103–105 °C). 1H NMR (400 MHz, CDCl3): δ = 7.42 (d, J = 8.7 Hz, 2 H), 7.32 (d, J = 8.7 Hz, 2 H), 6.89 (br s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 154.16, 135.34, 129.86, 129.29, 120.47. HRMS (EI): m/z calcd for C7H5ClN4O: 196.0152; found: 196.0156. Compound 3e (ref 15b): white solid; mp 96–97 °C (ref. 15b: 95–96 °C). 1H NMR (400 MHz, CDCl3): δ = 7.20–7.22 (m, 2 H), 6.87–6.88 (m, 1 H), 6.85 (br s, 1 H), 6.68–6.78 (m, 1 H), 3.82 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 160.27, 154.13, 138.13, 129.78, 111.58, 110.31, 105.33, 55.29. HRMS (EI): m/z calcd for C8H8N4O2: 192.0647; found: 192.0644.
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