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

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

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

We report Pd­(II)-catalyzed β-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 β-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