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B(C6F5)3‑Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

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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. 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.

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