Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets

Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation o...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 23; pp. 16535 - 16547
Main Authors Borlinghaus, Niginia, Schönfeld, Barbara, Heitz, Stephanie, Klee, Johanna, Vukelić, Stella, Braje, Wilfried M, Jolit, Anais
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 03.12.2021
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chemistry in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging.
AbstractList Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chemistry in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging.
Author Klee, Johanna
Braje, Wilfried M
Jolit, Anais
Vukelić, Stella
Heitz, Stephanie
Borlinghaus, Niginia
Schönfeld, Barbara
AuthorAffiliation Medicinal Chemistry Department, Neuroscience Discovery Research
AbbVie Deutschland GmbH & Co. KG
NCE Formulation Sciences
AuthorAffiliation_xml – name: AbbVie Deutschland GmbH & Co. KG
– name: Medicinal Chemistry Department, Neuroscience Discovery Research
– name: NCE Formulation Sciences
Author_xml – sequence: 1
  givenname: Niginia
  surname: Borlinghaus
  fullname: Borlinghaus, Niginia
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 2
  givenname: Barbara
  surname: Schönfeld
  fullname: Schönfeld, Barbara
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 3
  givenname: Stephanie
  surname: Heitz
  fullname: Heitz, Stephanie
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 4
  givenname: Johanna
  surname: Klee
  fullname: Klee, Johanna
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 5
  givenname: Stella
  surname: Vukelić
  fullname: Vukelić, Stella
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 6
  givenname: Wilfried M
  surname: Braje
  fullname: Braje, Wilfried M
  organization: AbbVie Deutschland GmbH & Co. KG
– sequence: 7
  givenname: Anais
  orcidid: 0000-0001-9810-9474
  surname: Jolit
  fullname: Jolit, Anais
  email: anais.jolit@abbvie.com
  organization: AbbVie Deutschland GmbH & Co. KG
BackLink https://www.ncbi.nlm.nih.gov/pubmed/34787429$$D View this record in MEDLINE/PubMed
BookMark eNp1kMtPAjEQhxuDkYeevZk9mpiFPrbd7tEgPhKMROC8KbuzsGRpse0m8t9bAnqzl0nbb36T-fqoo40GhG4JHhJMyUgVbrg1xZAUmEiRXqAe4RTHIsNJB_UwpjRmVLAu6ju3xeFwzq9QlyWpTBOa9ZCeaLVqar2O3sGrpjH7jfHGQmm-o7EKLwdXu6jW0UzZ8A1NNDdN62uj49lGOYjmB-03cISW7hjzVIfiYW2VP14_Qa1B-2gRpoB31-iyUo2Dm3MdoOXzZDF-jacfL2_jx2msGGM-rqjkspArwYBmCoigJRMphSQN24lSVLLknKYZSQpSSVakRGQriksiOIdEpmyA7k-5e2u-WnA-39WugKZRGkzrcsozyVmGOQ7o6IQW1jhnocr3tt4pe8gJzo-S8yA5D5Lzs-TQcXcOb1c7KP_4X6sBeDgBp87W6rDrv3E_HqqKHA
CitedBy_id crossref_primary_10_1002_anie_202209784
crossref_primary_10_1002_ange_202209784
crossref_primary_10_2174_1570193X19666220531153554
crossref_primary_10_1021_acs_joc_3c02351
Cites_doi 10.1038/nature14875
10.1126/science.aaf4622
10.1021/jacs.6b04818
10.1038/s41570-017-0052
10.1002/anie.201809431
10.1021/ja902046m
10.1126/science.aaw3254
10.1021/cc060089q
10.1021/acs.oprd.6b00161
10.1021/acscatal.9b00375
10.1021/ja512946e
10.1002/anie.201604429
10.1021/jo030005p
10.1021/acs.orglett.9b01423
10.1021/jacs.8b03744
10.1038/nature10647
10.1002/asia.201601487
10.1021/acs.joc.6b01449
10.1126/science.aag0209
10.1021/ol800548t
10.1016/j.trechm.2019.01.008
10.1021/ja301553c
10.1021/acs.joc.6b00800
10.1126/science.aat4133
10.1021/acs.joc.0c02576
10.1021/jo061420v
10.1134/s107042801304012x
10.1038/s41557-019-0254-5
10.1016/j.ejpb.2016.11.004
10.1002/anie.201709766
10.1002/adsc.201000476
10.1126/science.1253647
10.1021/acs.orglett.9b01016
10.1021/acsmedchemlett.0c00093
10.1038/s41557-018-0021-z
10.1021/acsmedchemlett.8b00183
10.1021/cc034019k
10.1126/science.aac9895
10.3109/10837450.2013.778869
10.1021/ol503043r
10.1021/acs.chemrev.6b00057
ContentType Journal Article
Copyright 2021 The Authors. Published by American Chemical Society
Copyright_xml – notice: 2021 The Authors. Published by American Chemical Society
DBID CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
DOI 10.1021/acs.joc.1c01867
DatabaseName Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
MEDLINE - Academic
DatabaseTitle MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
MEDLINE - Academic
DatabaseTitleList MEDLINE

Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 2
  dbid: EIF
  name: MEDLINE
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1520-6904
EndPage 16547
ExternalDocumentID 10_1021_acs_joc_1c01867
34787429
c707166001
Genre Journal Article
GroupedDBID -
29L
4.4
53G
55A
5RE
5VS
7~N
85S
AABXI
ABFLS
ABFRP
ABMVS
ABPPZ
ABPTK
ABUCX
ACGFS
ACJ
ACNCT
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
D0L
DU5
DZ
EBS
ED
F5P
GGK
GNL
IH2
IH9
IHE
JG
K2
LG6
P2P
PZZ
ROL
RXW
TAE
TN5
UI2
UKR
UPT
VF5
VG9
VQA
W1F
WH7
X
XFK
YZZ
---
-DZ
-~X
.K2
AAHBH
ABJNI
ABQRX
ACBEA
ACGFO
ADHLV
AGXLV
AHGAQ
CGR
CUPRZ
CUY
CVF
ECM
ED~
EIF
JG~
NPM
TAF
XSW
YQT
ZCA
AAYXX
CITATION
7X8
ID FETCH-LOGICAL-a333t-f2858c8b63e29ae162d3672e475206d6f8d5527914c1f83c7169b20d1655e4873
IEDL.DBID ACS
ISSN 0022-3263
IngestDate Fri Aug 16 08:07:13 EDT 2024
Fri Aug 23 04:03:36 EDT 2024
Sat Sep 28 08:22:10 EDT 2024
Mon Dec 06 03:12:30 EST 2021
IsPeerReviewed true
IsScholarly true
Issue 23
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a333t-f2858c8b63e29ae162d3672e475206d6f8d5527914c1f83c7169b20d1655e4873
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0001-9810-9474
PMID 34787429
PQID 2598539050
PQPubID 23479
PageCount 13
ParticipantIDs proquest_miscellaneous_2598539050
crossref_primary_10_1021_acs_joc_1c01867
pubmed_primary_34787429
acs_journals_10_1021_acs_joc_1c01867
PublicationCentury 2000
PublicationDate 20211203
2021-12-03
PublicationDateYYYYMMDD 2021-12-03
PublicationDate_xml – month: 12
  year: 2021
  text: 20211203
  day: 03
PublicationDecade 2020
PublicationPlace United States
PublicationPlace_xml – name: United States
PublicationTitle Journal of organic chemistry
PublicationTitleAlternate J. Org. Chem
PublicationYear 2021
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
References ref9/cit9
ref45/cit45
ref6/cit6
ref36/cit36
ref3/cit3
ref27/cit27
ref18/cit18
ref11/cit11
ref25/cit25
ref16/cit16
ref29/cit29
ref52/cit52
ref23/cit23
ref39/cit39
ref14/cit14
ref8/cit8
ref5/cit5
ref2/cit2
ref51/cit51
ref34/cit34
ref28/cit28
ref40/cit40
ref20/cit20
ref48/cit48
ref17/cit17
ref10/cit10
ref26/cit26
Raut R. (ref32/cit32) 2015; 5
ref35/cit35
ref19/cit19
ref21/cit21
ref12/cit12
ref15/cit15
ref46/cit46
ref22/cit22
ref49/cit49
ref13/cit13
ref33/cit33
ref4/cit4
ref30/cit30
ref47/cit47
ref1/cit1
ref24/cit24
ref7/cit7
ref50/cit50
References_xml – ident: ref39/cit39
  doi: 10.1038/nature14875
– ident: ref26/cit26
  doi: 10.1126/science.aaf4622
– ident: ref9/cit9
  doi: 10.1021/jacs.6b04818
– ident: ref5/cit5
  doi: 10.1038/s41570-017-0052
– ident: ref6/cit6
  doi: 10.1002/anie.201809431
– ident: ref46/cit46
  doi: 10.1021/ja902046m
– ident: ref52/cit52
  doi: 10.1126/science.aaw3254
– ident: ref22/cit22
  doi: 10.1021/cc060089q
– ident: ref27/cit27
  doi: 10.1021/acs.oprd.6b00161
– ident: ref45/cit45
  doi: 10.1021/acscatal.9b00375
– ident: ref30/cit30
  doi: 10.1021/ja512946e
– volume: 5
  start-page: 688
  year: 2015
  ident: ref32/cit32
  publication-title: Int. J. Pharm., Chem. Biol. Sci.
  contributor:
    fullname: Raut R.
– ident: ref40/cit40
  doi: 10.1002/anie.201604429
– ident: ref24/cit24
  doi: 10.1021/jo030005p
– ident: ref33/cit33
– ident: ref35/cit35
– ident: ref29/cit29
  doi: 10.1021/acs.orglett.9b01423
– ident: ref11/cit11
  doi: 10.1021/jacs.8b03744
– ident: ref15/cit15
  doi: 10.1038/nature10647
– ident: ref28/cit28
  doi: 10.1002/asia.201601487
– ident: ref3/cit3
  doi: 10.1021/acs.joc.6b01449
– ident: ref13/cit13
  doi: 10.1126/science.aag0209
– ident: ref51/cit51
  doi: 10.1021/ol800548t
– ident: ref1/cit1
  doi: 10.1016/j.trechm.2019.01.008
– ident: ref17/cit17
  doi: 10.1021/ja301553c
– ident: ref23/cit23
– ident: ref8/cit8
  doi: 10.1021/acs.joc.6b00800
– ident: ref16/cit16
  doi: 10.1126/science.aat4133
– ident: ref20/cit20
  doi: 10.1021/acs.joc.0c02576
– ident: ref25/cit25
  doi: 10.1021/jo061420v
– ident: ref50/cit50
  doi: 10.1134/s107042801304012x
– ident: ref12/cit12
  doi: 10.1038/s41557-019-0254-5
– ident: ref36/cit36
  doi: 10.1016/j.ejpb.2016.11.004
– ident: ref2/cit2
  doi: 10.1002/anie.201709766
– ident: ref49/cit49
  doi: 10.1002/adsc.201000476
– ident: ref10/cit10
  doi: 10.1126/science.1253647
– ident: ref48/cit48
  doi: 10.1021/acs.orglett.9b01016
– ident: ref19/cit19
  doi: 10.1021/acsmedchemlett.0c00093
– ident: ref7/cit7
  doi: 10.1038/s41557-018-0021-z
– ident: ref18/cit18
  doi: 10.1021/acsmedchemlett.8b00183
– ident: ref21/cit21
  doi: 10.1021/cc034019k
– ident: ref14/cit14
  doi: 10.1126/science.aac9895
– ident: ref34/cit34
  doi: 10.3109/10837450.2013.778869
– ident: ref47/cit47
  doi: 10.1021/ol503043r
– ident: ref4/cit4
  doi: 10.1021/acs.chemrev.6b00057
SSID ssj0000555
Score 2.4463258
Snippet Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and...
SourceID proquest
crossref
pubmed
acs
SourceType Aggregation Database
Index Database
Publisher
StartPage 16535
SubjectTerms Catalysis
Indicators and Reagents
Solubility
Tablets
Title Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets
URI http://dx.doi.org/10.1021/acs.joc.1c01867
https://www.ncbi.nlm.nih.gov/pubmed/34787429
https://search.proquest.com/docview/2598539050
Volume 86
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LS8QwEA4-Dnrx_VhfRNiDl65N0qTtUdYVEVbEXcFbSdMUV6UV2wX11zvTbndRET22hBBmknwzmZlvCGkbk8DdyFJHYWa7x43vhNzVDvONiZPQ50nVtK9_rS7vvKt7eT8ji_4ewefsVJui85ibDjMukq_Nk0UOqIh-1ll3MLt0pZRTYnCuxJTF58cECEOm-ApDv9iWFcZcrNbZWUVFTYipJU-dcRl3zMdP4sa_l79GViaWJj2rt8Y6mbPZBlnqNg3eNknWw7opgC7atyXG318ecvDAbZK_0S6-6iBZCR1l9Ea_YseVZ9q8oTk3DwB-dPCegfmIg6rEA3o-Khr2Cfy8tRrrtugQq7PKYovcXfSG3Utn0n7B0UKI0kl5IAMTxEpYHmrLFOhN-dx6vuSuSlQaJEjfFjLPsDQQBnl3Yu4mTElpwQ8S22QhyzO7S2gcY2_RUGsf3L0UPBwdSgOGlId8hCxhLdIGOUWT41NEVWScs6j-aaKJ8FrkpFFa9FKTcfw-9LhRagRixSiIzmw-LiLw98BECV3ptshOre3pZAKpigCh9_63nn2yzDHFBbNbxAFZKF_H9hBslDI-qnbnJ1qd3-8
link.rule.ids 315,786,790,2782,27107,27955,27956,57091,57141
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LT9wwEB5ROMClBQp0eRQjceCSJbZjJzmiBbQtLKJlkbhFjuOIlxJEslLh1zOT3SwqFRI9xrIsx2P7m_HMfAOwa22GdyPPPU2R7YGwoRcL33g8tDbN4lBkTdG-wZnuXwY_r9TVDPhtLgxOosKRqsaJ_8ouwPep7ba0XW594mD7BHMqRKwjZah38Xr3KqWm_OBCyymZzz8DEBrZ6m80ekfFbKDm-Av8mk6yiTC5647qtGuf3_A3_s9fLMLnid7JDsYbZQlmXLEM87223NtXKI4oiwqBjA1cTd74h-sS7XGXlX9Yj954iLqE3RTs3DxS_ZV71r6oeefXCIXs4qlAZZI6NWEI7PCmarko6PO3M5TFxYaUq1VXK3B5fDTs9b1JMQbPSClrLxeRimyUaulEbBzXKEUdCheESvg603mUEZlbzAPL80haYuFJhZ9xrZRDq0iuwmxRFu4bsDSlSqOxMSEafznaOyZWFtWqgNgJecY7sIvrlEwOU5U0fnLBk3GjTSaL14G9VnbJw5ia4_2uO61sE1xW8omYwpWjKkHrDxWW2Fd-B9bGQp8OJom4CPF6_WPz2Yb5_nBwmpz-ODvZgAVBwS8U9yI3YbZ-HLkt1F7q9HuzYV8A9anoWg
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3dT9wwDLc2Jm28wD7hgG2ZxMNeejRJk7aP6ODEPkCnwUm8VWmSCgZqT7Qnwf762b320JiQtsdGUeTaSWzH9s8Au9Y6vBt5EWjKbI-EjYNUhCbgsbW5S2Ph2qZ9xyf6aBp9PVfnXVEY1cIgETWuVLdBfDrVM1d0CAN8j8Z_VnbIbUg4bE_hmYp5RMdxf3R6f_8qpZYY4ULLJaDPXwuQRrL1nxrpETOzVTfjdZguCW2zTK6G8yYf2l8PMBz_909ewlpnf7L9xYZ5BU98-RpejPq2b2-gPKRqKlRo7Ng3FJWfXVTol3tX3bIRvfUQhAm7LNnE3FAflmvWv6wFkwtUiez0rkSjkia16Qjs4LLuMSno84c3VM3Fzqhmq6nfwnR8eDY6CrqmDIGRUjZBIRKV2CTX0ovUeK5RmjoWPoqVCLXTReII1C3lkeVFIi2h8eQidFwr5dE7ku9gpaxKvwksz6njaGpMjE5ggX6PSZVF8yoilELu-AB2kU9Zd6jqrI2XC54tBm3WMW8An3v5ZbMFRMfjUz_18s2QrRQbMaWv5nWGXiAaLmmowgFsLAS_XEwSgBHq7a1_o-cjPJ8cjLPvX06-bcOqoBwYSn-RO7DS3Mz9ezRimvxDu2d_A3-h6tQ
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=Enabling+Metallophotoredox+Catalysis+in+Parallel+Solution-Phase+Synthesis+Using+Disintegrating+Reagent+Tablets&rft.jtitle=Journal+of+organic+chemistry&rft.au=Borlinghaus%2C+Niginia&rft.au=Sch%C3%B6nfeld%2C+Barbara&rft.au=Heitz%2C+Stephanie&rft.au=Klee%2C+Johanna&rft.date=2021-12-03&rft.eissn=1520-6904&rft.volume=86&rft.issue=23&rft.spage=16535&rft.epage=16547&rft_id=info:doi/10.1021%2Facs.joc.1c01867&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon