B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
journal contributionposted on 17.04.2020, 14:46 by Shyam Basak, Ana Alvarez-Montoya, Laura Winfrey, Rebecca L Melen, Louis C Morrill, Alexander P Pulis
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.