4.8 Article

Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 9, Pages 2422-2427

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201308666

Keywords

alkyl Grignard reagents; breast cancer; enantiospecificity; Kumada coupling; nickel

Funding

  1. NIH NIGMS [R01GM100212]
  2. UC Cancer Research Coordinating Committee
  3. NCI [P30A062203, F31A177212]
  4. LaVerne Noyes Fellowship

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Alkyl Grignard reagents that contain beta-hydrogen atoms were used in a stereospecific nickel-catalyzed cross-coupling reaction to form C(sp(3))-C(sp(3)) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1-diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF-7 breast cancer cells.

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