4.6 Article

Palladium-Catalyzed ortho C-H Arylation of Benzaldehydes Using ortho-Sulfinyl Aniline as Transient Auxiliary

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 13, Issue 17, Pages 2423-2426

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800581

Keywords

2-methylsulfinyl aniline; benzaldehyde; C-H arylation; palladium; transient auxiliary

Funding

  1. Natural Science Foundation of China [21421062, 21502098, 21672105]
  2. Natural Science Foundation of Tianjin [17JCYBJC19700]
  3. State Key Laboratory of Elemento-Organic Chemistry at Nankai University

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A Pd-II-catalyzed ortho-(Csp(2))-H arylation reaction of benzaldehydes using a catalytic amount of 2-(methylsulfinyl)aniline as transient auxiliary was developed. This reaction is compatible with a broad range of benzaldehyde and aryl iodide substrates. Compared with other related reaction systems, an excellent regioselectivity for ortho-C(sp(2))-H bonds over benzylic C(sp(3))-H bonds was obtained for ortho-alkyl-benzaldehyde substrates.

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