4.8 Article

Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 45, Pages 16080-16083

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b09761

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Funding

  1. Scripps Research Institute
  2. NIH (NIGMS) [2R01GM084019]
  3. Boehringer Ingelheim Fellowship

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We report Pd(II)-catalyzed beta-C(sp(3)) -H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported beta-C(sp(3))-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl (hetero)aryl coupling involving both primary and secondary alkyls.

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