Palladium-Catalyzed Cross-Coupling Reactions of Potassium N-Methyltrifluoroborate Isoindolin-1-one with Aryl and Heteroaryl Chlorides

Abstract

Potassium N-methyltrifluoroborate isoindolin-1-one was synthesized and used in Suzuki–Miyaura palladium-catalyzed cross-coupling reactions with aryl and heteroaryl chlorides to prepare 29 examples of substituted N-benzyl isoindolin-1-ones. The new approach benefits from mild reaction conditions that tolerate a variety of functional groups. In addition, because of the large number of commercially available aryl and heteroaryl chlorides that can serve as coupling partners, the approach readily provides access to libraries of substituted N-benzyl isoindolin-1-ones.

GRAPHICAL ABSTRACT

Keywords:

• Isoindolinone
• methylaminotrifluoroborates
• organotrifluoroborates
• palladium-catalyzed cross-coupling
• potassium N-methyltrifluoroborate isoindolin-1-one
• Suzuki–Miyaura cross-coupling

Notes

^a Reaction conditions: 1.0 equiv. of aryl chloride; 1.2 equiv. of trifluoroborate 6; isolated yields after silica gel column chromatography or preparative TLC.

^a Reaction conditions: 1.0 equiv. of heteroaryl chloride; 1.2 equiv. of trifluoroborate 6; isolated yields after silica gel column chromatography or preparative TLC.

^a Reaction conditions: 1.0 equiv. of aryl chloride; 1.2 equiv. of trifluoroborate 6; isolated yields after silica gel column chromatography or preparative TLC.

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