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

ABSTRACT: The first example of palladium(II)-catalyzed ?-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 ?-functional groups, as well as alkenes and alkynes, and rapid access to diverse sterically hindered quaternary centers.

SUBMITTER: Zhu RY

PROVIDER: S-EPMC5710739 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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

Zhu Ru-Yi RY Liu Luo-Yan LY Yu Jin-Quan JQ

Journal of the American Chemical Society 20170829 36

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 ...[more]

PMID: 28844134

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