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

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

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...

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Bibliographic Details
Published in:ACS catalysis Vol. 10; no. 8; pp. 4835 - 4840
Main Authors: Basak, Shyam, Alvarez-Montoya, Ana, Winfrey, Laura, Melen, Rebecca L, Morrill, Louis C, Pulis, Alexander P
Format: Journal Article
Language:English
Published: American Chemical Society 17-04-2020
Subjects:
Letter
boranes
oxindoles
catalysis
alkylation
indoles
N-heterocycles
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c01141