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Synlett 2018; 29(10): 1400-1404
DOI: 10.1055/s-0036-1591970
DOI: 10.1055/s-0036-1591970
letter
Remote Oxidative C–H Amidation of Anilides with Dibenzenesulfonimides under Metal-Free Conditions
We are grateful to the National Natural Science Foundation of China (No. 21702054), Hubei Provincial Natural Science Foundation (No. 2016CFB206) and the Hubei Provincial Hundred-Talent Program Fund for financial support.Weitere Informationen
Publikationsverlauf
Received: 17. Dezember 2017
Accepted after revision: 05. März 2018
Publikationsdatum:
07. Mai 2018 (online)
Abstract
A remote oxidative C–H bond amidation of anilides with dibenzenesulfonimides mediated by PhI(OAc)2 under metal-free conditions provided para-amidated anilides with high selectivity and moderate to good yields. The reaction proceeded under mild or neutral conditions and it has good air and moisture tolerance. The method represents a novel and facile strategy for the synthesis of arylamines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591970.
- Supporting Information
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- 11 N-{4-[Bis(phenylsulfonyl)amino]-2-methylphenyl}acetamide (3a); Typical Procedure A vial containing a stirring bar and sealed with a Teflon-lined cap was charged with a mixture of 2-methylacetanilide (1a, 0.2 mmol), PhI(OAc)2 (0.4 mmol), and HN(SO2Ph)2 (2a, 0.3mmol). THF (2 mL) was added, and the mixture was stirred at 25 °C for 8 h. The mixture was then added to H2O (15 mL), and the resulting mixture was extracted with EtOAc (3 × 10 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography [silica gel, EtOAc–PE (2:1)] to give a white solid; yield: 64.0 mg (72%); mp 184–186 °C. 1H NMR (400 MHz, CDCl3): δ = 2.14 (s, 3 H), 2.18 (s, 3 H), 6.79–6.84 (m, 2 H), 7.21 (s, 1 H), 7.54 (t, J = 7.54 Hz, 4 H), 7.67 (t, J = 7.36 Hz, 2 H), 7.92 (d, J = 7.92 Hz, 4 H), 7.98 (d, J = 8.48 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 7.63, 24.57, 122.40, 128.52, 129.06, 129.81, 130.09, 133.23, 133.53, 134.03, 137.86, 139.30, 168.52. HRMS-ESI: m/z [M + H]+ calcd for C21H21N2O5S2: 445.0886; found: 445.0884.
For selected reviews, see:
For examples of transition-metal-catalyzed para-C–H amination, see:
For a recent review, see:
For recent reviews, see: