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. 2017 Sep 13;139(36):12394-12397.
doi: 10.1021/jacs.7b06851. Epub 2017 Aug 29.

Highly Versatile β-C(sp3)-H Iodination of Ketones Using a Practical Auxiliary

Ru-Yi Zhu  1 , Luo-Yan Liu  1 , Jin-Quan Yu  1
Affiliations

Highly Versatile β-C(sp3)-H Iodination of Ketones Using a Practical Auxiliary

Ru-Yi Zhu et al. J Am Chem Soc. .

Abstract

The first example of palladium(II)-catalyzed β-C(sp3)-H iodination of a wide range of ketones using a commercially available aminooxyacetic acid auxiliary has been achieved. This L, X-type directing group overcomes the limitations of the transient directing group approach for C(sp3)-H functionalization of ketones. Practical advantages of this method include simple installation of the auxiliary without chromatography, exceptional tolerance of α-functional groups, as well as alkenes and alkynes, and rapid access to diverse sterically hindered quaternary centers.

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Figures

Scheme 1
Scheme 1
Transient and Covalent Directing Groups based on Amino acids
Scheme 2
Scheme 2
Rational Design of a Powerful Directing Group
Scheme 3
Scheme 3
Incompatible Ketone Substrates with O-Methyl Oxime Directing Group
Scheme 4
Scheme 4
Characterization of the Palladacycle
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