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Synlett 2017; 28(15): 2000-2003
DOI: 10.1055/s-0036-1588422
DOI: 10.1055/s-0036-1588422
letter
In situ Generation and Utilization of CO: An Efficient Route towards N-Substituted Saccharin via Carbonylative Cyclization of 2-Iodosulfonamides
Further Information
Publication History
Received: 25 February 2017
Accepted after revision: 20 April 2017
Publication Date:
18 May 2017 (online)
Abstract
The present protocol demonstrates the synthesis of N-substituted saccharines via carbonylative cyclization of 2-iodosulfonamides using a Pd(OAc)2/Xantphos catalyst system and phenyl formate as a CO source. A variety of saccharin derivatives is synthesized under milder reaction conditions.
Key words
carbonylative cyclization - palladium catalysis - CO surrogate - phenyl formate - N-substituted saccharin.Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588422.
- Supporting Information
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- 21 General Experimental Procedure for the Synthesis of N-Substituted Saccharins An oven-dried Schlenk tube was charged with Pd(OAc)2 (6.7 mg, 0.03 mmol), Xantphos (34.7 mg, 0.06 mmol), 2-iodosulfonamide (1.0 mmol), phenyl formate (1.5 mmol), and Et3N (3 mmol) under nitrogen, and the reaction mixture was stirred at 80 °C for 18 h. The reaction mixture was then diluted with EtOAc (10 mL) and aq NaHCO3 (10 mL), and the aqueous phase was further extracted with EtOAc (3 × 20 mL). The combined organic layers washed with brine, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (120–200 mesh) using EtOAc–PE as eluents to give the corresponding N-substituted saccharin 3a–o. Compound 3a: isolated as white solid; 238 mg (92%). 1H NMR (500 MHz, CDCl3): δ = 8.16 (d, J = 7.6 Hz, 1 H), 8.02–7.98 (m, 1 H), 7.95–7.86 (m, 2 H), 7.59–7.52 (m, 5 H). 13C NMR (126 MHz, CDCl3): δ = 158.3, 137.6, 135.0, 134.4, 130.1, 129.9, 128.7, 128.6. 127.1, 125.6, 121.2. Compound 3h: isolated as white solid; 249 mg (90%). 1H NMR (500 MHz, CDCl3): δ = 8.15 (d, J = 7.6 Hz, 1 H), 7.99 (d, J = 7.4 Hz, 1 H), 7.95–7.86 (m, 2 H), 7.54–7.49 (m, 1 H), 7.36 (d, J = 7.6 Hz, 1 H), 7.30 (dt, J = 9.1, 2.2 Hz, 1 H), 7.24–7.20 (m, 1 H). 13C NMR (126 MHz, CDCl3): δ = 163.9, 161.9, 158.0, 137.4, 135.2, 134.6, 131.0, 130.9, 130.1, 130.0, 126.8, 125.7, 124.0, 124.0, 121.2, 117.2, 117.1, 116.0, 115.8. Compound 3m: isolated as white solid; 245 mg (90%). 1H NMR (500 MHz, CDCl3): δ = 8.04 (d, J = 7.6 Hz, 1 H), 7.91 (d, J = 7.4 Hz, 1 H), 7.86–7.78 (m, 2 H), 7.50 (d, J = 7.3 Hz, 2 H), 7.37–7.29 (m, 3 H), 4.90 (s, 2 H). 13C NMR (126 MHz, CDCl3): δ = 158.8, 137.7, 134.7, 134.4, 134.3, 128.7, 128.6, 128.2, 127.2, 125.2, 121.0, 42.6.