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

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journal contribution
posted on 17.04.2020, 14:46 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.

Funding

SB, RLM, and LCM gratefully acknowledge the School of Chemistry, Cardiff University for generous support and the Leverhulme Trust for a Research Project Grant (RPG-2015-361). RLM would like to acknowledge the EPSRC for a research fellowship (EP/R026912/1). AAM, LW and APP thanks the School of Chemistry, University of Leicester for their generous support and the Royal Society for a Research Grant(RGS\R1\191082)

History

Citation

ACS Catal. 2020, 10, 8, 4835-4840

Version

AM (Accepted Manuscript)

Published in

ACS Catalysis

Pagination

4835 - 4840

Publisher

American Chemical Society (ACS)

issn

2155-5435

eissn

2155-5435

Copyright date

2020

Available date

09/04/2020

Publisher version

https://pubs.acs.org/doi/abs/10.1021/acscatal.0c01141?

Language

en