B(C6F5)3-catalyzed direct C3 alkylation of indoles and oxindoles

Basak, Shyam, Alvarez-Montoya, Ana, Winfrey, Laura, Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 and Pulis, Alexander P. 2020. B(C6F5)3-catalyzed direct C3 alkylation of indoles and oxindoles. ACS Catalysis 10 (8) , pp. 4835-4840. 10.1021/acscatal.0c01141

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	American Chemical Society
ISSN:	2155-5435
Funders:	EPSRC, Leverhulme Trust and the Royal Society
Date of First Compliant Deposit:	17 April 2020
Date of Acceptance:	2 April 2020
Last Modified:	03 May 2023 11:05
URI:	https://orca.cardiff.ac.uk/id/eprint/131072

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