AI Article Synopsis
- A novel three-component reaction method is introduced for arylboration of alkenyl amines using a cleavable picolinamide directing group.
- This approach effectively utilizes aryl halides and BPin to transform a variety of alkenes into functionalized boryl aliphatic amines with excellent chemo- and regiocontrol.
- The resulting pinacol boronic ester group allows for further chemical transformations, suggesting potential applications for diverse regioselective modifications of alkenyl amines.
Article Abstract
We report herein a three-component 1,2-arylboration of alkenyl amines bearing a cleavable picolinamide directing group. With aryl halides as electrophiles and BPin as nucleophiles, a wide range of alkenes could be converted into valuable boryl-functionalized aliphatic amines. The reaction proceeds with high levels of chemo- and regiocontrol and exhibits high functional group tolerance. In addition, the pinacol boronic ester group could undergo various transformations, indicating that the protocol could potentially provide a platform for versatile regioselective difunctionalization of alkenyl amines.
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| http://dx.doi.org/10.1021/acs.orglett.2c02768 | DOI Listing |
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Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
Article Synopsis
- A novel three-component reaction method is introduced for arylboration of alkenyl amines using a cleavable picolinamide directing group.
- This approach effectively utilizes aryl halides and BPin to transform a variety of alkenes into functionalized boryl aliphatic amines with excellent chemo- and regiocontrol.
- The resulting pinacol boronic ester group allows for further chemical transformations, suggesting potential applications for diverse regioselective modifications of alkenyl amines.
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