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Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

ABSTRACT: We report a general protocol for ortho-C-H fluoroalkoxylation of benzaldehydes and benzylic amines utilizing an inexpensive amino amide as a transient directing group. In the presence of an electrophilic fluorinating bystanding oxidant and fluorinated alcohols, a wide range of benzaldehydes and benzylic amines could be oxygenated selectively at the ortho positions to afford fluoroalkyl aryl ethers. This elegant approach would provide appealing strategies for synthesis of drug molecules and natural products.

SUBMITTER: Tian M

PROVIDER: S-EPMC9235058 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

Tian Mixiang M Shao Lidong L Su Xiaosan X Zhou Xuhong X Zhang Honglei H Wei Kun K Sun Ruifen R Wang Junliang J

RSC advances 20220627 29

We report a general protocol for ortho-C-H fluoroalkoxylation of benzaldehydes and benzylic amines utilizing an inexpensive amino amide as a transient directing group. In the presence of an electrophilic fluorinating bystanding oxidant and fluorinated alcohols, a wide range of benzaldehydes and benzylic amines could be oxygenated selectively at the ortho positions to afford fluoroalkyl aryl ethers. This elegant approach would provide appealing strategies for synthesis of drug molecules an ...[more]

PMID: 35873337

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