B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
journal contributionposted on 2020-04-17, 14:46 authored 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.
SB, RLM, and LCM gratefully acknowledge the School of Chemistry, Cardiff University for generous support and the Leverhulme Trust for a Research Project Grant (RPG-2015-361). RLM would like to acknowledge the EPSRC for a research fellowship (EP/R026912/1). AAM, LW and APP thanks the School of Chemistry, University of Leicester for their generous support and the Royal Society for a Research Grant(RGS\R1\191082)
CitationACS Catal. 2020, 10, 8, 4835-4840
- AM (Accepted Manuscript)