Employing Pd-Catalyzed C–H Arylation in Multicomponent-Multicatalyst Reactions (MC)2R: One-Pot Synthesis of Dihydrobenzoquinolines

The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh­(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd­(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reactio...

Full description

Saved in:
Bibliographic Details
Published inACS catalysis Vol. 7; no. 2; pp. 1378 - 1382
Main Authors Lied, Fabian, Brodnik Žugelj, Helena, Kress, Steffen, Štefane, Bogdan, Glorius, Frank, Lautens, Mark
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.02.2017
Subjects
enantioselectivity
C−H functionalization
chemoselectivity
heterocycles
multicatalytic reactions
Online AccessGet full text

Cover

Abstract The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh­(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd­(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reaction (MC)2R could be used to develop an efficient and step-economic protocol for the rapid construction of molecular complexity. A high-yielding synthesis of π-extended heteroarenes through an efficient three-step-one-pot procedure and a highly enantioselective synthesis of 6-alkylsubstituted dihydrobenzoquinolines are shown.
AbstractList The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh­(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd­(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reaction (MC)2R could be used to develop an efficient and step-economic protocol for the rapid construction of molecular complexity. A high-yielding synthesis of π-extended heteroarenes through an efficient three-step-one-pot procedure and a highly enantioselective synthesis of 6-alkylsubstituted dihydrobenzoquinolines are shown.
Author Brodnik Žugelj, Helena
Kress, Steffen
Lautens, Mark
Lied, Fabian
Glorius, Frank
Štefane, Bogdan
AuthorAffiliation Davenport Research Laboratories, Department of Chemistry
Organisch-Chemisches Institut
Westfälische Wilhelms-Universität Münster
University of Ljubljana
University of Toronto
Faculty of Chemistry and Chemical Technology
AuthorAffiliation_xml – name: Westfälische Wilhelms-Universität Münster
– name: Organisch-Chemisches Institut
– name: University of Ljubljana
– name: Davenport Research Laboratories, Department of Chemistry
– name: University of Toronto
– name: Faculty of Chemistry and Chemical Technology
Author_xml – sequence: 1
  givenname: Fabian
  surname: Lied
  fullname: Lied, Fabian
– sequence: 2
  givenname: Helena
  surname: Brodnik Žugelj
  fullname: Brodnik Žugelj, Helena
– sequence: 3
  givenname: Steffen
  surname: Kress
  fullname: Kress, Steffen
– sequence: 4
  givenname: Bogdan
  surname: Štefane
  fullname: Štefane, Bogdan
– sequence: 5
  givenname: Frank
  orcidid: 0000-0002-0648-956X
  surname: Glorius
  fullname: Glorius, Frank
  email: glorius@uni-muenster.de
– sequence: 6
  givenname: Mark
  surname: Lautens
  fullname: Lautens, Mark
  email: mlautens@chem.utoronto.ca
BookMark eNpNkM9OAjEQxhuDiYjcPfaoicX-ZXe9kRXFBAJBPW-63SIlS4u0HJaTB9_AN_RJ3BVMnMvMZGa-L_M7By3rrAbgkuAewZTcSuWVDLLs9XPMKE5OQJsSIZDgTLT-1Weg6_0K18FFP45wG3wO15vSVca-wVmB0kak2usCpt8fXyM42FalDMZZaCyc7MpglFtvam8b0KH9PfABzrVUzaKHV5P0ms7v4NRqNHMBPlc2LLU3HroFvDfLqti6XNu9e98Z60pjtb8ApwtZet095g54fRi-pCM0nj4-pYMxkoTSgJKcc5LnXEexTlS_EJLVP0VYcimiiLOEkDhJYkVlQRlXiWJFvqBCq3rMo4KzDrg56Na8spXbbW3tlhGcNRCzP4jZESL7AUkZa4A
ContentType Journal Article
Copyright Copyright © 2017 American Chemical Society
Copyright_xml – notice: Copyright © 2017 American Chemical Society
DOI 10.1021/acscatal.6b03209
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2155-5435
EndPage 1382
ExternalDocumentID b650362232
GroupedDBID 53G
55A
7~N
AABXI
ABMVS
ABUCX
ACGFS
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
EBS
ED
ED~
EJD
GNL
IH9
JG
JG~
RNS
ROL
UI2
VF5
VG9
W1F
ID FETCH-LOGICAL-a122t-9b441bb4e78e9c6d5a343570a4a577439118998c2ad234c9c3dbf25eca5747d43
IEDL.DBID ACS
ISSN 2155-5435
IngestDate Thu Aug 27 13:42:36 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 2
Keywords enantioselectivity
C−H functionalization
chemoselectivity
heterocycles
multicatalytic reactions
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a122t-9b441bb4e78e9c6d5a343570a4a577439118998c2ad234c9c3dbf25eca5747d43
ORCID 0000-0002-0648-956X
PageCount 5
ParticipantIDs acs_journals_10_1021_acscatal_6b03209
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
7~N
VG9
W1F
ACS
AEESW
AFEFF
ABMVS
ABUCX
IH9
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 20170203
PublicationDateYYYYMMDD 2017-02-03
PublicationDate_xml – month: 02
  year: 2017
  text: 20170203
  day: 03
PublicationDecade 2010
PublicationTitle ACS catalysis
PublicationTitleAlternate ACS Catal
PublicationYear 2017
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
SSID ssj0000456870
Score 2.331657
Snippet The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the...
SourceID acs
SourceType Publisher
StartPage 1378
Title Employing Pd-Catalyzed C–H Arylation in Multicomponent-Multicatalyst Reactions (MC)2R: One-Pot Synthesis of Dihydrobenzoquinolines
URI http://dx.doi.org/10.1021/acscatal.6b03209
Volume 7
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LS8QwEA4-DnrxLb7JQUEPWbdp0m68SVUWwQe7Ct5KXsVF6IKph-7Jg__Af-gvcdJ2VdTDHks7JUwSvm-SmfkQ2m9z1RY0zghwjYwA3gZEcsGJClnHRkZxEfgC56vrqHvPLh_4w3ebnN83-DQ4ltpVJxmtSHmxbzGNZmkMe8PToKT_dZ7iqUmn0oYDEOOEAw1obiX_-4nHIu1-IMnFYi1J5KoGhD6B5Kn1UqiWHv1tzzjBIJfQQkMo8Wm9ApbRlM1X0Fwy1nFbRW-1qC9AFL41JPH25cganHy8vnfBrqyz4fAgx1U1rk8yH-aARaR-rAxcgXu2roFw-PAqOaK9E3yTW3I7LHC_zIFGuoHDwwyfDR5L42uM8hFgziD3okDWraH7i_O7pEsa7QUiA0oLIhTMm1LMxh0rdGS4DMGjcVsyyWMfxEBgApGaptLQkGmhQ6Myyq2G1yw2LFxHMzkMdgPhQGlOI6p8fRczKpKShZKHmbDSRkKrTXQA7kubvePS6lqcBunYp2nj060Jv9tG89Rjr0-tDnfQTPH8YneBORRqr1oyn88EwQw
link.rule.ids 315,783,787,27088,27936,27937,57070,57120
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LT9wwELYoHOilvFqVlocPIJWDtxvHTtbcUGC1LSxd7UPaW-RX1AgpK9XhsHviwD_gH_JLGCdZWiEO5ZjHWKPJRN83nhkPQkdtrtqCxhkBrpERwNuASC44USHr2MgoLgLf4Ny_jnoT9nPKpysoWPbCgBIOVnJVEv_v6QLBd7hXbWi0IuVnfot3aI3H4K-eDSWj520Vz1A61Yg4wDJOOLCBJjn52iIekrT7B1C6G2j4rEpVR3LTui1VSy9enNL4Jl030YeGXuKz2h-20IotttF6spzqtoPu6xG_AFh4YEji5ecLa3DyePfQA7l5XRuH8wJXvbm-5HxWADKR-rIScCUe2rojwuFv_eSEDk_xr8KSwazEo3kBpNLlDs8yfJ7_nhvfcVQsAIHywo8Isu4jmnQvxkmPNJMYiAwoLYlQ8BWVYjbuWKEjw2UIho3bkkke-5AGwhSI2zSVhoZMCx0alVFuNTxmsWHhJ7RagLKfEQ6U5jSiynd7MaMiKVkoeZgJK20ktNpFx2C-tPmTXFolyWmQLm2aNjb98p_vHaL13rh_lV79uL78it5Tj8q-6DrcQ6vln1u7D5yiVAeVFz0Box_JbA
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LT-MwELagSMAFWGDFc_FhkeDg0jh2UnNDgaqwC1S8xC3yK9oKKUU4HNoTB_4B_3B_CeMkRQhxgGMeY43Gtr4Zz4w_hH63uGoJGmcEfI2MAN4GRHLBiQpZ20ZGcRH4BufTs6h7zU5u-e0E4uNeGFDCwUiuTOL7XX1vsvqGgWAP3peHGs1Ied5vMYmmeBxQz9hwkFy-Ha14L6Vd0sQBnnHCwSOoE5SfDeJhSbt3oNKZRzdv6pS1JHfNx0I19ejDTY3f1ncBzdVuJj6o1sUPNGHzRTSTjNndltBzRfULwIV7hiRefjiyBif_n166IDesauRwP8dlj64vPR_kgFCkeiwFXIEvbNUZ4fDOabJLL_bxeW5Jb1Dgy2EOzqXrOzzI8GH_39D4zqN8BEjUzz1VkHXL6LpzdJV0Sc3IQGRAaUGEgtlUitm4bYWODJchGDduSSZ57EMbCFcgftNUGhoyLXRoVEa51fCZxYaFP1EjB2VXEA6U5jSiynd9MaMiKVkoeZgJK20ktFpF22C-tN5RLi2T5TRIxzZNa5uuffG_LTTdO-ykf4_P_qyjWerB2ddehxuoUTw82k1wLQr1q1xIryLgy-Y
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Employing+Pd-Catalyzed+C%E2%80%93H+Arylation+in+Multicomponent-Multicatalyst+Reactions+%28MC%292R%3A+One-Pot+Synthesis+of+Dihydrobenzoquinolines&rft.jtitle=ACS+catalysis&rft.au=Lied%2C+Fabian&rft.au=Brodnik+Z%CC%8Cugelj%2C+Helena&rft.au=Kress%2C+Steffen&rft.au=S%CC%8Ctefane%2C+Bogdan&rft.date=2017-02-03&rft.pub=American+Chemical+Society&rft.issn=2155-5435&rft.eissn=2155-5435&rft.volume=7&rft.issue=2&rft.spage=1378&rft.epage=1382&rft_id=info:doi/10.1021%2Facscatal.6b03209&rft.externalDocID=b650362232
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2155-5435&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2155-5435&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2155-5435&client=summon