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Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids.

ABSTRACT: Three-component carboamination of alkenes is of significant interest due to the ease by which functionalized amines can be produced from readily available chemical building blocks. Previously, a variety of carbon-centered radical precursors have been studied as the carbon components for this reaction, however, the use of general alkyl sources has remained as an unsolved challenge. Herein we present our efforts to develop an oxidative carboamination protocol that utilizes alkylboronic acids as carbon-centered radical precursors. The presented work demonstrates 34 examples, ranging from 17 to 88% yields, with a broad scope in vinylarenes, amines, and alkylboronic acids. Preliminary mechanistic studies suggest that a single-electron oxidation of the alkylboronic acid generates a carbon-centered radical intermediate that adds across the olefin followed by C-N bond formation via Cu-mediated inner-sphere or carbocation-mediated pathways.

SUBMITTER: Gockel SN

PROVIDER: S-EPMC9815720 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids.

Gockel Samuel N SN Lee SangHyun S Gay Brittany L BL Hull Kami L KL

ACS catalysis 20210414 9

Three-component carboamination of alkenes is of significant interest due to the ease by which functionalized amines can be produced from readily available chemical building blocks. Previously, a variety of carbon-centered radical precursors have been studied as the carbon components for this reaction, however, the use of general alkyl sources has remained as an unsolved challenge. Herein we present our efforts to develop an oxidative carboamination protocol that utilizes alkylboronic acids as ca ...[more]

PMID: 36619299

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