B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
Shyam Basak, Ana Alvarez-Montoya, Laura Winfrey, Rebecca L. Melen, Louis C. Morrill, Alexander P. Pulis
Abstract
The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C-H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade.
Topics & Concepts
AlkylationHeterolysisCatalysisChemistryBoranesAmine gas treatingBoraneCleavage (geology)Combinatorial chemistryRing (chemistry)Organic chemistryMedicinal chemistryMaterials scienceBoronComposite materialFracture (geology)Organoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions