B(3,4,5-F3H2C6)3 Lewis acid-catalysed C3-allylation of indoles

Nusaybah Alotaibi; Rasool Babaahmadi; Milan Pramanik; Tanja Kaehler; Ayan Dasgupta; Emma Richards; Alireza Ariafard; Thomas Wirth; Rebecca L. Melen

doi:10.1039/D3DT00745F

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B(3,4,5-F₃H₂C₆)₃ Lewis acid-catalysed C3-allylation of indoles†

Nusaybah Alotaibi,

^a Rasool Babaahmadi,

^a Milan Pramanik,^a Tanja Kaehler,^a Ayan Dasgupta,^ab Emma Richards,

^a Alireza Ariafard,

^c Thomas Wirth

^d and Rebecca L. Melen

*^a

Author affiliations

* Corresponding authors

^a Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, Maindy Road, Cathays, Cardiff, Cymru/Wales, UK
E-mail: MelenR@cardiff.ac.uk

^b Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK

^c School of Natural Sciences (Chemistry), University of Tasmania, Private Bag 75, Hobart, Tasmania, 7001 Australia

^d School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales, UK

Abstract

Herein we report the B(3,4,5-F₃H₂C₆)₃-catalysed C3-allylation of indoles using allylic esters. 25 examples of C3-allylated products are presented in up to 97% yield. The mechanism for the reaction was explored using detailed Density Functional Theory (DFT) studies.

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Article information

DOI: https://doi.org/10.1039/D3DT00745F
Article type: Communication
Submitted: 10 Mar 2023
Accepted: 10 Apr 2023
First published: 11 Apr 2023
This article is Open Access

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Dalton Trans., 2023,52, 5039-5043

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B(3,4,5-F₃H₂C₆)₃ Lewis acid-catalysed C3-allylation of indoles

N. Alotaibi, R. Babaahmadi, M. Pramanik, T. Kaehler, A. Dasgupta, E. Richards, A. Ariafard, T. Wirth and R. L. Melen, Dalton Trans., 2023, 52, 5039 DOI: 10.1039/D3DT00745F

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