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

Handle URI:
http://hdl.handle.net/10754/604381
Title:
Catalytic α-arylation of imines leading to N-unprotected indoles and azaindoles
Authors:
Marelli, Enrico; Corpet, Martin; Minenkov, Yury; Neyyappadath, Rifahath; Bismuto, Alessandro; Buccolini, Giulia; Curcio, Massimiliano; Cavallo, Luigi ( 0000-0002-1398-338X ) ; Nolan, Steven P.
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.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)
Citation:
Catalytic α-arylation of imines leading to N-unprotected indoles and azaindoles 2016 ACS Catalysis
Publisher:
American Chemical Society (ACS)
Journal:
ACS Catalysis
Issue Date:
30-Mar-2016
DOI:
10.1021/acscatal.6b00040
Type:
Article
ISSN:
2155-5435; 2155-5435
Sponsors:
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).
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acscatal.6b00040
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorMarelli, Enricoen
dc.contributor.authorCorpet, Martinen
dc.contributor.authorMinenkov, Yuryen
dc.contributor.authorNeyyappadath, Rifahathen
dc.contributor.authorBismuto, Alessandroen
dc.contributor.authorBuccolini, Giuliaen
dc.contributor.authorCurcio, Massimilianoen
dc.contributor.authorCavallo, Luigien
dc.contributor.authorNolan, Steven P.en
dc.date.accessioned2016-04-04T14:19:35Zen
dc.date.available2016-04-04T14:19:35Zen
dc.date.issued2016-03-30en
dc.identifier.citationCatalytic α-arylation of imines leading to N-unprotected indoles and azaindoles 2016 ACS Catalysisen
dc.identifier.issn2155-5435en
dc.identifier.issn2155-5435en
dc.identifier.doi10.1021/acscatal.6b00040en
dc.identifier.urihttp://hdl.handle.net/10754/604381en
dc.description.abstractA 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.en
dc.description.sponsorshipWe 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).en
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acscatal.6b00040en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acscatal.6b00040.en
dc.titleCatalytic α-arylation of imines leading to N-unprotected indoles and azaindolesen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalACS Catalysisen
dc.eprint.versionPost-printen
dc.contributor.institutionSchool of Chemistry, EaStCHEM, University of St Andrews, North Haugh, St. Andrews KY16 9ST , U.K.en
dc.contributor.institutionChemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabiaen
dc.contributor.institutionDepartment of Inorganic and Physical Chemistry, Universiteit Gent, Krijgslaan 281 - S3, 9000 Ghent, Belgiumen
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)en
kaust.authorMinenkov, Yuryen
kaust.authorCavallo, Luigien
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