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Synlett 2017; 28(15): 2030-2035
DOI: 10.1055/s-0036-1588437
DOI: 10.1055/s-0036-1588437
letter
Pd/C-Catalyzed Homocoupling Reaction for the Synthesis of Symmetrical Biaryl Diamides
This work was financially supported by the National Natural Science Foundation of China (No. 21402079) and the Research Fund for the Doctoral Program of Liaocheng University (No. 318051403 and 318051419).Further Information
Publication History
Received: 17 March 2017
Accepted after revision: 04 May 2017
Publication Date:
24 May 2017 (online)
Abstract
Pd/C was found to be an efficient and convenient metal catalyst in the homocoupling reaction for the synthesis of symmetrical biaryl diamides. The catalyst system Pd/C–KOAc showed high catalytic activity, and a variety of symmetrical biaryl diamides were conveniently synthesized from 2-halo-N-phenylbenzamides in moderate to good yields.
Key words
Pd/C - homocoupling reaction - symmetrical biaryl diamides - 2-halo-N-phenylbenzamides - recyclabilitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588437.
- Supporting Information
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- 20 General Procedure for the Synthesis of Symmetrical Biaryl Diamides An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, 10% Pd/C (10% wt% of a), 2-halo-N-phenylbenzamides a (0.3 mmol) and KOAc (0.6 mmol). The tube was placed under vacuum for 20 min and backfilled with N2. Then DMA (2.0 mL) was added through a syringe. The reaction mixture was stirred at 125 °C for 20 h. The reaction was monitored by TLC. When 2-halo-N-phenylbenzamides a consumed completely, the reaction was stopped and cooled to r.t., EtOAc (40 mL) was added, and the mixture was washed with brine (3 × 20 mL). The organic phase was dried over Na2SO4 and concentrated. The residue was purified directly by column chromatography on silica gel to give the pure products b (PE–EtOAc = 2:1, v/v). Typical Analytical Data of N 2,N 2′-Diphenyl-[1,1′-biphenyl]-2,2′-dicarboxamide (1b) 1H NMR (400 MHz, CDCl3): δ = 9.00 (s, 2 H), 7.69 (d, J = 7.2 Hz, 2 H), 7.45–7.58 (m, 8 H), 7.26 (t, J = 7.6 Hz, 4 H), 7.17 (d, J = 8.4 Hz, 2 H), 7.07 (t, J = 7.2 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 168.46, 139.21, 138.03, 136.20, 130.34, 129.86, 129.04, 128.27, 127.33, 124.61, 120.08.
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