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Functionalized polychloroarenes in the Bichwald ligand-promoted Suzuki cross-coupling

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Abstract

Palladium-catalyzed Suzuki cross-coupling of isomeric dichloroacetophenones with phenylboronic acid in the presence of 2-dicyclohexylphosphino-2′-(dimethylamino)-biphenyl (DavePHOS, a Buchwald ligand) affords the corresponding diphenylacetophenones in high yields. The reaction of pentachloroacetophenone with phenylboronic acid (1.1–2.5 equiv.) proceeds unselectively to give isomeric mono- and disubstitution products. In the case of 3,4-dichloroanisole, 3-positioned chlorine atom is preferably replaced, however, with excess phenylboronic acid 4′;-methoxy-1,1′;:2′;,1″-terphenyl is quantitatively formed.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. A. Vasil’ev, A. S. Burukin, G. M. Zhdankina & S. G. Zlotin

Authors
  1. A. A. Vasil’ev
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  2. A. S. Burukin
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  3. G. M. Zhdankina
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  4. S. G. Zlotin
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Corresponding author

Correspondence to A. A. Vasil’ev.

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Dedicated to Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1656–1661, August, 2022.

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Vasil’ev, A.A., Burukin, A.S., Zhdankina, G.M. et al. Functionalized polychloroarenes in the Bichwald ligand-promoted Suzuki cross-coupling. Russ Chem Bull 71, 1656–1661 (2022). https://doi.org/10.1007/s11172-022-3575-2

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  • DOI: https://doi.org/10.1007/s11172-022-3575-2

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