Ruthenium(II)-Catalyzed [4 + 2] Electro-Oxidative Annulation of C 6‑Arylpurines/Purine Nucleosides

A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C 6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol described herein exhibits high regioselectivity, broad scope,...

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Published inOrganic letters Vol. 25; no. 37; pp. 6796 - 6801
Main Authors Yang, Qi-Liang, Luo, Yi-Rui, Xu, Rong-Yi, Zhang, Bei-Ning, Zhang, Yan-Ni, Guo, Hai-Ming
Format Journal Article
LanguageEnglish
Published American Chemical Society 22.09.2023
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Abstract A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C 6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol described herein exhibits high regioselectivity, broad scope, and wide functional group tolerance, allowing efficient coupling of various biologically important molecules including acyclic, ribosyl, arabinosyl, and deoxyribosyl purine nucleoside derivatives. A novel purinoisoquinolinium-coordinated ruthenium(0) sandwich intermediate has been isolated, crystallographically characterized, and electrochemically analyzed, offering direct mechanistic insight.
AbstractList A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C 6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol described herein exhibits high regioselectivity, broad scope, and wide functional group tolerance, allowing efficient coupling of various biologically important molecules including acyclic, ribosyl, arabinosyl, and deoxyribosyl purine nucleoside derivatives. A novel purinoisoquinolinium-coordinated ruthenium(0) sandwich intermediate has been isolated, crystallographically characterized, and electrochemically analyzed, offering direct mechanistic insight.
Author Luo, Yi-Rui
Yang, Qi-Liang
Zhang, Bei-Ning
Xu, Rong-Yi
Zhang, Yan-Ni
Guo, Hai-Ming
AuthorAffiliation State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering
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Cites_doi 10.1021/acscatal.5b00243
10.1021/acscatal.8b00373
10.1021/acs.orglett.6b03772
10.1021/acscatal.9b04125
10.1039/D2GC03218J
10.2174/1385272823666191023122704
10.1002/anie.201509316
10.31635/ccschem.020.202000365
10.1021/acs.orglett.7b00478
10.1021/jacs.5b04858
10.1021/acs.orglett.5b01247
10.1021/acscentsci.0c01413
10.1016/j.tet.2014.12.066
10.31635/ccschem.021.202101451
10.1002/anie.201707714
10.1080/15257770903054159
10.1021/ja404414q
10.2174/138161213804805711
10.1002/chem.201300155
10.1039/D2QO00904H
10.1021/acscatal.5b01244
10.1002/asia.202300060
10.3390/molecules20059419
10.1039/D1CC05590A
10.1039/D2CC00172A
10.1039/C8CC05743E
10.1021/acs.orglett.8b02068
10.1021/acs.orglett.5b00355
10.1039/D1SC04011A
10.2174/1568026616666160829155805
10.1021/acs.orglett.6b03314
10.1002/ijch.201300010
10.1039/D2CC03625H
10.1021/acs.joc.8b01077
10.1038/nrd4010
10.1021/acs.orglett.2c01546
10.1021/acs.orglett.6b01055
10.1021/jo070518m
10.1021/acs.orglett.0c04168
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References ref9/cit9
ref6/cit6
ref19/cit19b
ref16/cit16
Mukherjee K. (ref20/cit20e) 2022
ref8/cit8a
ref8/cit8b
ref21/cit21b
ref21/cit21c
ref21/cit21a
ref2/cit2b
ref2/cit2a
ref1/cit1a
ref1/cit1b
ref5/cit5b
ref17/cit17
ref5/cit5c
ref10/cit10
ref5/cit5a
ref18/cit18b
ref18/cit18c
ref18/cit18a
ref14/cit14a
ref12/cit12
ref14/cit14c
ref14/cit14b
ref15/cit15
ref3/cit3b
ref11/cit11b
ref3/cit3a
ref11/cit11a
ref20/cit20a
ref22/cit22
ref13/cit13
ref20/cit20c
ref20/cit20b
ref20/cit20d
ref4/cit4
ref19/cit19a
ref7/cit7
References_xml – ident: ref10/cit10
  doi: 10.1021/acscatal.5b00243
– ident: ref19/cit19a
  doi: 10.1021/acscatal.8b00373
– volume-title: Handbook of CH-Functionalization
  year: 2022
  ident: ref20/cit20e
  contributor:
    fullname: Mukherjee K.
– ident: ref6/cit6
  doi: 10.1021/acs.orglett.6b03772
– ident: ref14/cit14c
  doi: 10.1021/acscatal.9b04125
– ident: ref21/cit21c
  doi: 10.1039/D2GC03218J
– ident: ref5/cit5c
  doi: 10.2174/1385272823666191023122704
– ident: ref7/cit7
  doi: 10.1002/anie.201509316
– ident: ref18/cit18a
  doi: 10.31635/ccschem.020.202000365
– ident: ref11/cit11b
  doi: 10.1021/acs.orglett.7b00478
– ident: ref11/cit11a
  doi: 10.1021/jacs.5b04858
– ident: ref12/cit12
  doi: 10.1021/acs.orglett.5b01247
– ident: ref17/cit17
  doi: 10.1021/acscentsci.0c01413
– ident: ref3/cit3b
  doi: 10.1016/j.tet.2014.12.066
– ident: ref19/cit19b
  doi: 10.31635/ccschem.021.202101451
– ident: ref14/cit14a
  doi: 10.1002/anie.201707714
– ident: ref1/cit1a
  doi: 10.1080/15257770903054159
– ident: ref8/cit8a
  doi: 10.1021/ja404414q
– ident: ref5/cit5a
  doi: 10.2174/138161213804805711
– ident: ref9/cit9
  doi: 10.1002/chem.201300155
– ident: ref21/cit21b
  doi: 10.1039/D2QO00904H
– ident: ref8/cit8b
  doi: 10.1021/acscatal.5b01244
– ident: ref18/cit18c
  doi: 10.1002/asia.202300060
– ident: ref2/cit2b
  doi: 10.3390/molecules20059419
– ident: ref4/cit4
  doi: 10.1039/D1CC05590A
– ident: ref20/cit20d
  doi: 10.1039/D2CC00172A
– ident: ref14/cit14b
  doi: 10.1039/C8CC05743E
– ident: ref20/cit20b
  doi: 10.1021/acs.orglett.8b02068
– ident: ref22/cit22
  doi: 10.1021/acs.orglett.5b00355
– ident: ref16/cit16
  doi: 10.1039/D1SC04011A
– ident: ref5/cit5b
  doi: 10.2174/1568026616666160829155805
– ident: ref20/cit20a
  doi: 10.1021/acs.orglett.6b03314
– ident: ref3/cit3a
  doi: 10.1002/ijch.201300010
– ident: ref18/cit18b
  doi: 10.1039/D2CC03625H
– ident: ref20/cit20c
  doi: 10.1021/acs.joc.8b01077
– ident: ref1/cit1b
  doi: 10.1038/nrd4010
– ident: ref15/cit15
  doi: 10.1021/acs.orglett.2c01546
– ident: ref13/cit13
  doi: 10.1021/acs.orglett.6b01055
– ident: ref2/cit2a
  doi: 10.1021/jo070518m
– ident: ref21/cit21a
  doi: 10.1021/acs.orglett.0c04168
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