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

doi:10.1021/acscatal.6b00040

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 journal › Article › peer-review

28 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 language	English (US)
Pages (from-to)	2930-2938
Number of pages	9
Journal	ACS Catalysis
Volume	6
Issue number	5
DOIs	https://doi.org/10.1021/acscatal.6b00040
State	Published - 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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10.1021/acscatal.6b00040

https://repository.kaust.edu.sa/bitstream/10754/604381/1/acscatal2E6b00040.pdf

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title = "Catalytic α-arylation of imines leading to N-unprotected indoles and azaindoles",

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.",

author = "Enrico Marelli and Martin Corpet and Yury Minenkov and Rifahath Neyyappadath and Alessandro Bismuto and Giulia Buccolini and Massimiliano Curcio and Luigi Cavallo and Nolan, {Steven P.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Dr. Jos{\`e} A. F{\`e}rnandez-S{\`a}las, 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).",

year = "2016",

month = apr,

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doi = "10.1021/acscatal.6b00040",

language = "English (US)",

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T1 - Catalytic α-arylation of imines leading to N-unprotected indoles and azaindoles

AU - Marelli, Enrico

AU - Corpet, Martin

AU - Minenkov, Yury

AU - Neyyappadath, Rifahath

AU - Bismuto, Alessandro

AU - Buccolini, Giulia

AU - Curcio, Massimiliano

AU - Cavallo, Luigi

AU - Nolan, Steven P.

N1 - 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).

PY - 2016/4/7

Y1 - 2016/4/7

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/604381

UR - http://pubs.acs.org/doi/abs/10.1021/acscatal.6b00040

UR - http://www.scopus.com/inward/record.url?scp=84973621376&partnerID=8YFLogxK

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EP - 2938

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -

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

Abstract

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