Visible-light-induced C–H alkylation of pyridine derivatives via 1,2-hydrogen atom transfer

A visible-light-induced radical–radical cross-coupling protocol between hydroxamic acid derivatives and pyridine derivatives for the synthesis of pyridin-2-ylmethanamine derivatives via 1,2-hydrogen atom transfer has been reported. This protocol features metal-free and mild reaction conditions, a br...

Full description

Saved in:
Bibliographic Details
Published inCatalysis science & technology Vol. 15; no. 13; pp. 3940 - 3945
Main Authors Ye, Meiling, Tian, Zeyu, Li, Yuanyuan, Wang, Hang, Huang, Tianle, Yang, Zhongzhen, Wu, Yong
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 30.06.2025
Subjects
Alkylation
Cross coupling
Functional groups
Hydrogen atoms
Pyridines
Radicals
Online AccessGet full text

Cover

Abstract A visible-light-induced radical–radical cross-coupling protocol between hydroxamic acid derivatives and pyridine derivatives for the synthesis of pyridin-2-ylmethanamine derivatives via 1,2-hydrogen atom transfer has been reported. This protocol features metal-free and mild reaction conditions, a broad range of substrates, remarkable functional group tolerance and potential application.
AbstractList A visible-light-induced radical–radical cross-coupling protocol between hydroxamic acid derivatives and pyridine derivatives for the synthesis of pyridin-2-ylmethanamine derivatives via 1,2-hydrogen atom transfer has been reported. This protocol features metal-free and mild reaction conditions, a broad range of substrates, remarkable functional group tolerance and potential application.
Author Wu, Yong
Tian, Zeyu
Li, Yuanyuan
Yang, Zhongzhen
Wang, Hang
Huang, Tianle
Ye, Meiling
Author_xml – sequence: 1
  givenname: Meiling
  orcidid: 0009-0005-0166-0048
  surname: Ye
  fullname: Ye, Meiling
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
– sequence: 2
  givenname: Zeyu
  surname: Tian
  fullname: Tian, Zeyu
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
– sequence: 3
  givenname: Yuanyuan
  surname: Li
  fullname: Li, Yuanyuan
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
– sequence: 4
  givenname: Hang
  surname: Wang
  fullname: Wang, Hang
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
– sequence: 5
  givenname: Tianle
  surname: Huang
  fullname: Huang, Tianle
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
– sequence: 6
  givenname: Zhongzhen
  surname: Yang
  fullname: Yang, Zhongzhen
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China, Department of Pharmacy, West China Hospital, Sichuan University, Chengdu, Sichuan 610041, China
– sequence: 7
  givenname: Yong
  orcidid: 0000-0003-0719-4963
  surname: Wu
  fullname: Wu, Yong
  organization: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China
BookMark eNpFkMtKAzEUhoNUsNZufIKAO3E0t5k0yzJeKhTcqOBChmSStKnTpCbTwux8B9_QJ3GkomfzH34-zoHvGAx88AaAU4wuMaLi6jovXxBilE0PwJAgxjLGCzz423N6BMYprVA_TGA0IUPw-uySU43JGrdYtpnzelsbDcuvj88ZlM1b18jWBQ-DhZsuOu28gdpEt-vrnUlw5yTEFyRbdjqGhfFQtmEN2yh9siaegEMrm2TGvzkCT7c3j-Usmz_c3ZfTeVYTgtqMT3KcI5QzIZBgGNdC5DXFRHDFEDVKWGKI1YoXShOrmDIMSctNrRnnBbd0BM72dzcxvG9NaqtV2Ebfv6woITntqQL11PmeqmNIKRpbbaJby9hVGFU_Bqt_g_Qb7Clkzg
Cites_doi 10.1038/s41586-020-2213-0
10.1021/acs.jmedchem.4c01122
10.1021/cr400008h
10.1021/acs.chemrev.9b00214
10.1002/anie.202108775
10.1021/acs.orglett.8b02737
10.1002/cjoc.202400122
10.1021/jacs.3c04376
10.1126/science.1213920
10.1097/COH.0000000000000713
10.1021/acs.orglett.4c02742
10.1021/acs.orglett.3c03523
10.1002/adsc.202400642
10.1021/acscatal.0c04519
10.1021/cr940474e
10.1126/science.aaf6635
10.1021/acs.accounts.5b00068
10.1016/0009-2614(86)80542-5
10.1038/s41557-018-0021-z
10.1039/D3GC01426F
10.1021/acs.orglett.0c02659
10.1002/anie.201811004
10.1002/anie.202302941
10.1358/dot.2019.55.6.2984806
10.1002/anie.202208018
10.1021/cr900382t
10.1039/D2RA01571D
10.1126/science.1255525
10.1055/a-1300-3453
10.1055/a-1390-9065
ContentType Journal Article
Copyright Copyright Royal Society of Chemistry 2025
Copyright_xml – notice: Copyright Royal Society of Chemistry 2025
DBID AAYXX
CITATION
7SR
8BQ
8FD
JG9
DOI 10.1039/D5CY00434A
DatabaseName CrossRef
Engineered Materials Abstracts
METADEX
Technology Research Database
Materials Research Database
DatabaseTitle CrossRef
Materials Research Database
Engineered Materials Abstracts
Technology Research Database
METADEX
DatabaseTitleList CrossRef
Materials Research Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2044-4761
EndPage 3945
ExternalDocumentID 10_1039_D5CY00434A
GroupedDBID 0-7
0R~
705
AAEMU
AAIWI
AAJAE
AANOJ
AARTK
AAWGC
AAXHV
AAYXX
ABASK
ABDVN
ABEMK
ABJNI
ABPDG
ABRYZ
ABXOH
ACAYK
ACGFS
ACIWK
ACLDK
ADMRA
ADSRN
AEFDR
AENEX
AENGV
AESAV
AETIL
AFLYV
AFOGI
AFRZK
AFVBQ
AGEGJ
AGRSR
AHGCF
AKBGW
AKMSF
ALMA_UNASSIGNED_HOLDINGS
ANUXI
APEMP
ASKNT
AUDPV
BLAPV
BSQNT
C6K
CITATION
EBS
ECGLT
EE0
EF-
GGIMP
H13
HZ~
H~N
J3I
O-G
O9-
OK1
R7G
RAOCF
RCNCU
RNS
RPMJG
RRC
RSCEA
RVUXY
SKA
SKF
SKH
SKJ
SKM
SKR
SKZ
SLC
SLF
SLH
7SR
8BQ
8FD
JG9
ID FETCH-LOGICAL-c220t-7851500549909411c995c31297b403eb9f2e2fdb76bd2fb4be40af7ecd47767f3
ISSN 2044-4753
IngestDate Mon Jun 30 10:53:50 EDT 2025
Thu Jul 03 08:17:00 EDT 2025
IsPeerReviewed true
IsScholarly true
Issue 13
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c220t-7851500549909411c995c31297b403eb9f2e2fdb76bd2fb4be40af7ecd47767f3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ORCID 0009-0005-0166-0048
0000-0003-0719-4963
PQID 3225377660
PQPubID 2047527
PageCount 6
ParticipantIDs proquest_journals_3225377660
crossref_primary_10_1039_D5CY00434A
PublicationCentury 2000
PublicationDate 2025-06-30
PublicationDateYYYYMMDD 2025-06-30
PublicationDate_xml – month: 06
  year: 2025
  text: 2025-06-30
  day: 30
PublicationDecade 2020
PublicationPlace Cambridge
PublicationPlace_xml – name: Cambridge
PublicationTitle Catalysis science & technology
PublicationYear 2025
Publisher Royal Society of Chemistry
Publisher_xml – name: Royal Society of Chemistry
References Hou (D5CY00434A/cit11/1) 2024; 26
Yus (D5CY00434A/cit2b/1) 2013; 113
Chen (D5CY00434A/cit9a/1) 2018; 20
Cao (D5CY00434A/cit4b/1) 2023; 62
Zhang (D5CY00434A/cit12a/1) 2020; 22
Yang (D5CY00434A/cit1b/1) 2022; 61
Wu (D5CY00434A/cit3b/1) 2019; 119
Tang (D5CY00434A/cit10c/1) 2024; 42
Dvory-Sobol (D5CY00434A/cit6a/1) 2022; 17
Blakemore (D5CY00434A/cit1a/1) 2018; 10
Bloch (D5CY00434A/cit3a/1) 1998; 98
Shaw (D5CY00434A/cit8d/1) 2016; 352
De (D5CY00434A/cit4a/1) 2022; 12
Beatty (D5CY00434A/cit8a/1) 2015; 48
Wu (D5CY00434A/cit12b/1) 2019; 58
Leng (D5CY00434A/cit7/1) 2020; 10
Robak (D5CY00434A/cit2a/1) 2010; 110
Kumar (D5CY00434A/cit3c/1) 2020; 581
Ferrero Desideri (D5CY00434A/cit6b/1) 2019; 55
Zuo (D5CY00434A/cit8c/1) 2014; 345
Wayner (D5CY00434A/cit13/1) 1986; 131
Li (D5CY00434A/cit15b/1) 2024; 366
Marshall (D5CY00434A/cit5/1) 2024; 67
Li (D5CY00434A/cit9c/1) 2023; 25
Wu (D5CY00434A/cit14/1) 2022; 33
Keum (D5CY00434A/cit9b/1) 2021; 60
McNally (D5CY00434A/cit8b/1) 2011; 334
Chen (D5CY00434A/cit15a/1) 2023; 25
Liu (D5CY00434A/cit10a/1) 2021; 32
Jiang (D5CY00434A/cit10b/1) 2023; 145
References_xml – volume: 581
  start-page: 415
  year: 2020
  ident: D5CY00434A/cit3c/1
  publication-title: Nature
  doi: 10.1038/s41586-020-2213-0
– volume: 67
  start-page: 11622
  year: 2024
  ident: D5CY00434A/cit5/1
  publication-title: J. Med. Chem.
  doi: 10.1021/acs.jmedchem.4c01122
– volume: 113
  start-page: 5595
  year: 2013
  ident: D5CY00434A/cit2b/1
  publication-title: Chem. Rev.
  doi: 10.1021/cr400008h
– volume: 119
  start-page: 11245
  year: 2019
  ident: D5CY00434A/cit3b/1
  publication-title: Chem. Rev.
  doi: 10.1021/acs.chemrev.9b00214
– volume: 60
  start-page: 25235
  year: 2021
  ident: D5CY00434A/cit9b/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.202108775
– volume: 20
  start-page: 6255
  year: 2018
  ident: D5CY00434A/cit9a/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.8b02737
– volume: 42
  start-page: 2203
  year: 2024
  ident: D5CY00434A/cit10c/1
  publication-title: Chin. J. Chem.
  doi: 10.1002/cjoc.202400122
– volume: 145
  start-page: 16045
  year: 2023
  ident: D5CY00434A/cit10b/1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/jacs.3c04376
– volume: 334
  start-page: 1114
  year: 2011
  ident: D5CY00434A/cit8b/1
  publication-title: Science
  doi: 10.1126/science.1213920
– volume: 17
  start-page: 15
  year: 2022
  ident: D5CY00434A/cit6a/1
  publication-title: Curr. Opin. HIV AIDS
  doi: 10.1097/COH.0000000000000713
– volume: 26
  start-page: 7638
  year: 2024
  ident: D5CY00434A/cit11/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.4c02742
– volume: 25
  start-page: 9124
  year: 2023
  ident: D5CY00434A/cit15a/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.3c03523
– volume: 366
  start-page: 4436
  year: 2024
  ident: D5CY00434A/cit15b/1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.202400642
– volume: 10
  start-page: 13196
  year: 2020
  ident: D5CY00434A/cit7/1
  publication-title: ACS Catal.
  doi: 10.1021/acscatal.0c04519
– volume: 98
  start-page: 1407
  year: 1998
  ident: D5CY00434A/cit3a/1
  publication-title: Chem. Rev.
  doi: 10.1021/cr940474e
– volume: 352
  start-page: 1304
  year: 2016
  ident: D5CY00434A/cit8d/1
  publication-title: Science
  doi: 10.1126/science.aaf6635
– volume: 48
  start-page: 1474
  year: 2015
  ident: D5CY00434A/cit8a/1
  publication-title: Acc. Chem. Res.
  doi: 10.1021/acs.accounts.5b00068
– volume: 131
  start-page: 189
  year: 1986
  ident: D5CY00434A/cit13/1
  publication-title: Chem. Phys. Lett.
  doi: 10.1016/0009-2614(86)80542-5
– volume: 10
  start-page: 383
  year: 2018
  ident: D5CY00434A/cit1a/1
  publication-title: Nat. Chem.
  doi: 10.1038/s41557-018-0021-z
– volume: 25
  start-page: 5030
  year: 2023
  ident: D5CY00434A/cit9c/1
  publication-title: Green Chem.
  doi: 10.1039/D3GC01426F
– volume: 22
  start-page: 7315
  year: 2020
  ident: D5CY00434A/cit12a/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.0c02659
– volume: 58
  start-page: 1774
  year: 2019
  ident: D5CY00434A/cit12b/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.201811004
– volume: 62
  start-page: e202302941
  year: 2023
  ident: D5CY00434A/cit4b/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.202302941
– volume: 55
  start-page: 377
  year: 2019
  ident: D5CY00434A/cit6b/1
  publication-title: Drugs Today
  doi: 10.1358/dot.2019.55.6.2984806
– volume: 61
  start-page: e202208018
  year: 2022
  ident: D5CY00434A/cit1b/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.202208018
– volume: 110
  start-page: 3600
  year: 2010
  ident: D5CY00434A/cit2a/1
  publication-title: Chem. Rev.
  doi: 10.1021/cr900382t
– volume: 12
  start-page: 15385
  year: 2022
  ident: D5CY00434A/cit4a/1
  publication-title: RSC Adv.
  doi: 10.1039/D2RA01571D
– volume: 345
  start-page: 437
  year: 2014
  ident: D5CY00434A/cit8c/1
  publication-title: Science
  doi: 10.1126/science.1255525
– volume: 32
  start-page: 356
  year: 2021
  ident: D5CY00434A/cit10a/1
  publication-title: Synlett
  doi: 10.1055/a-1300-3453
– volume: 33
  start-page: 1154
  year: 2022
  ident: D5CY00434A/cit14/1
  publication-title: Synlett
  doi: 10.1055/a-1390-9065
SSID ssj0000491082
Score 2.412807
Snippet A visible-light-induced radical–radical cross-coupling protocol between hydroxamic acid derivatives and pyridine derivatives for the synthesis of...
SourceID proquest
crossref
SourceType Aggregation Database
Index Database
StartPage 3940
SubjectTerms Alkylation
Cross coupling
Functional groups
Hydrogen atoms
Pyridines
Radicals
Title Visible-light-induced C–H alkylation of pyridine derivatives via 1,2-hydrogen atom transfer
URI https://www.proquest.com/docview/3225377660
Volume 15
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1bb9MwFLbK9gAviKsYDGQJ3kpG6ksSP5awUcEYLy1rkVAUx45WEdqpSyaFJ_4AT_xDfgnHSZxkokLAS9Q6qhP5fD03fz4HoWfU514cC9_xKZcQoKTaibknHGPbuJCem1R5yHcn3mTG3sz5fDD43mMtFbk8SL5uPVfyP1KFMZCrOSX7D5JtJ4UB-AzyhStIGK5_JeMPSwB0pp2sqgYC0XVhdvNDS2Cgk2GcfS6z1is8LzdLZdxKBW93WZX8vhheLuMhqLOQOGel2qzhYUMIxL-Y5hHg0jbk3baWQd7UMLHHgQxy8t_S84s6362XmbWMFdO3TrZ-1GXR8oAqMsGiAJVUdDg9bZLYk7j5dZOWINxy6Fo-k0l-WOZpxSxp-td1Co64jDnMr4sFH-j-WF2gvdXQvI9E2tO3pq97z3bDV77VLrjUlFVVPCnN1ifrWT-743_yPjqaHR9H08P59BraJRB1gNrcHb99-fq0TdpBODVyqwZk7bvbkrdUvOimv-rkXLXxleMyvYVuNhEHHtfwuY0GenUHXW8X6i76tBVGOPz57ccEdwDC6xRbAOEegDAACI-ed_DBBj7Ywucemh0dTsOJ03TdcBJC3NzxwQfnxpMHP0Ww0SgRgicU3EJfMpdqKVKiSaqk70lFUsmkZm6c-jpRzFSGSul9tLNar_QDhINABYQqxbhQEBhwmFESL_ADkXgpi-keemqXKTqvi6tEFSmCiugVDxfVYo730L5dwaj5811Exg5ReJ7nPvzz7UfoRgfPfbSTbwr9GPzIXD5ppPsLVnt0Sg
linkProvider Royal Society of Chemistry
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=Visible-light-induced+C%E2%80%93H+alkylation+of+pyridine+derivatives+via+1%2C2-hydrogen+atom+transfer&rft.jtitle=Catalysis+science+%26+technology&rft.au=Ye%2C+Meiling&rft.au=Tian%2C+Zeyu&rft.au=Li%2C+Yuanyuan&rft.au=Wang%2C+Hang&rft.date=2025-06-30&rft.pub=Royal+Society+of+Chemistry&rft.issn=2044-4753&rft.eissn=2044-4761&rft.volume=15&rft.issue=13&rft.spage=3940&rft.epage=3945&rft_id=info:doi/10.1039%2Fd5cy00434a&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2044-4753&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2044-4753&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2044-4753&client=summon