cs0c01141_si_001.pdf (15.33 MB)
B(C6F5)3‑Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
journal contribution
posted on 2020-04-09, 12:04 authored by Shyam Basak, Ana Alvarez-Montoya, Laura Winfrey, Rebecca L. Melen, Louis C. Morrill, Alexander P. PulisThe
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.