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Palladium-Mediated C_γ -H Functionalization of Alicyclic Amines.

ABSTRACT: This paper describes a new method for the transannular functionalization of the γ-C-H bonds in alicyclic amines to install C(sp³ )-halogen, oxygen, nitrogen, boron, and sulfur bonds. The key challenge for this transformation is controlling the relative rate of C_γ -H versus C_α -H functionalization. We demonstrate that this selectivity can be achieved by pre-complexation of the substrate with Pd prior to the addition of oxidant. This approach enables the use of diverse oxidants that ultimately install various heteroatom functional groups at the γ-position with high site- and diastereoselectivity.

SUBMITTER: Aguilera EY

PROVIDER: S-EPMC8102420 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Palladium-Mediated Cγ -H Functionalization of Alicyclic Amines.

Aguilera Ellen Y EY Sanford Melanie S MS

Angewandte Chemie (International ed. in English) 20210408 20

This paper describes a new method for the transannular functionalization of the γ-C-H bonds in alicyclic amines to install C(sp3 )-halogen, oxygen, nitrogen, boron, and sulfur bonds. The key challenge for this transformation is controlling the relative rate of Cγ -H versus Cα -H functionalization. We demonstrate that this selectivity can be achieved by pre-complexation of the substrate with Pd prior to the addition of oxidant. This approach enables the use of div ...[more]

PMID: 33720500

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