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

ABSTRACT: We report Pd(II)-catalyzed ?-C(sp3)-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 ?-C(sp3)-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.

SUBMITTER: Zhu RY 

PROVIDER: S-EPMC5710734 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp<sup>3</sup>)-H Activation.

Zhu Ru-Yi RY   Liu Luo-Yan LY   Park Han Seul HS   Hong Kai K   Wu Yongwei Y   Senanayake Chris H CH   Yu Jin-Quan JQ  

Journal of the American Chemical Society 20171103 45

We report Pd(II)-catalyzed β-C(sp<sup>3</sup>)-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 β-C(sp<sup>3</sup>)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl co  ...[more]

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