Catalytic α-arylation of imines leading to N-unprotected indoles and azaindoles

Enrico Marelli, Martin Corpet, Yury Minenkov, Rifahath Neyyappadath, Alessandro Bismuto, Giulia Buccolini, Massimiliano Curcio, Luigi Cavallo, Steven P. Nolan

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

A Palladium-N-heterocyclic carbene-catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reactions pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point towards a deprotonative mechanism being operative.
Original languageEnglish (US)
Pages (from-to)2930-2938
Number of pages9
JournalACS Catalysis
Volume6
Issue number5
DOIs
StatePublished - Apr 7 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Dr. Josè A. Fèrnandez-Sàlas, Dr. Fady Nahra, and
Dr. Marcel Brill for useful discussions. Dr. Sunil V. Sharma,
Dr. Cristina Pubil and Dr. Rebecca J. M. Goss are gratefully acknowledged for the help provided during the revision of
this manuscript. We thank ERC (FUNCAT to SPN) for funding.
We thank the EPSRC NMSSC in Swansea for mass spectrometric
analyses. The EPSRC is gratefully acknowledged
for financial support (Ph.D. studentships to AB, GB, MC and
RMN Through the doctoral training centre CRITICAT
EP/L016419/1).

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