B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles | Zendy

Shyam Basak | Zendy; Ana Alvarez-Montoya | Zendy; Laura Winfrey | Zendy; Rebecca L. Melen | Zendy; Louis C. Morrill | Zendy; Alexander P. Pulis | Zendy

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

Author(s) -

Shyam Basak,

Ana Alvarez-Montoya,

Laura Winfrey,

Rebecca L. Melen,

Louis C. Morrill,

Alexander P. Pulis

Publication year - 2020

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.0c01141

Subject(s) - alkylation , heterolysis , catalysis , chemistry , boranes , amine gas treating , borane , cleavage (geology) , combinatorial chemistry , ring (chemistry) , organic chemistry , medicinal chemistry , materials science , boron , composite material , fracture (geology)

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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