4.8 Article

Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 33, Pages 11355-11359

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905174

Keywords

asymmetric catalysis; cross-coupling; phosphorus ligands; palladium; transmetalation

Funding

  1. CAS [QYZDY-SSW-SLH029] Funding Source: Medline
  2. NSFC [21725205, 21432007, 21572246] Funding Source: Medline
  3. Science and Technology Commission of Shanghai Municipality [18520712200] Funding Source: Medline
  4. K.C. Wong Education Foundation [0000] Funding Source: Medline
  5. the Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000] Funding Source: Medline

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We herein report an enantioselective palladium-catalyzed cross-coupling between alpha-bromo carboxamides and aryl boronic acids, generating a series of chiral alpha-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of alpha-bromo carbonyl compounds.

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