4.7 Article

Pd(TFA)2-catalyzed direct arylation of quinoxalinones with arenes

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 2, Pages 231-235

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo01250d

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSIT) [2018R1A2B2004432]
  2. Priority Research Centers Program [2014R1A6A1031189]
  3. Nano Material Technology Development Program of the Korean National Research Foundation (NRF) - Korean Ministry of Education, Science, and Technology [2012M3A7B4049675]

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The direct C-3 arylation of quinoxalin-2-ones with arenes is achieved by a Pd(TFA)(2)-catalyzed cross-dehydrogenative coupling (CDC) reaction. A wide array of functionalities, including highly sensitive allyl- and benzyl group substituted quinoxalin-2(H)-ones, are readily assembled with arenes containing electron-donating and electron-withdrawing groups in this CDC reaction. Highly regioselective products are produced in good yields with stronger electron-donating groups than toluene and densely substituted arenes as coupling partners. This protocol represents an efficient technique to access various 3-aryl-benzo[g]quinoxalinones and 2-aryl-4-methylpyrido[3,4-b]pyrazin-3(4H)-ones under mild conditions.

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