Photocatalytic Substrate Oxidation Catalyzed by a Ruthenium(II) Complex with a Phenazine Moiety as the Active Site Using Dioxygen as a Terminal Oxidant
We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e–-oxidized products without the reductive activation of O2 in acidic water under visible-light irradiation. A RuII complex (1) bearing a pyrazine moiety as the active site in tetrapyrido...
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| Published in | Journal of the American Chemical Society Vol. 146; no. 48; pp. 33022 - 33034 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
04.12.2024
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/jacs.4c09962 |
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| Abstract | We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e–-oxidized products without the reductive activation of O2 in acidic water under visible-light irradiation. A RuII complex (1) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1-H+, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1-H+ was converted to the corresponding dihydro-intermediate (2-H+), where the pyrazine moiety of the ligand received 2e– and 2H+ from the substrate. 2-H+ was facilely oxidized by O2 to recover 1-H+. Consequently, an oxidation product of the substrate and H2O2 derived from dioxygen reduction were obtained; however, the H2O2 formed was also used for oxidation of 2-H+. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1-H+ was achieved in neither the lowest singlet excited state nor triplet excited state (S1 or T1) but in the second lowest singlet excited state (S2), i.e., 1(π–π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1-H+ can be categorized into unusual anti-Kasha photocatalysis. |
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| AbstractList | We have developed photocatalytic oxidation of aromatic substrates using O
as a terminal oxidant to afford only 2e
-oxidized products without the reductive activation of O
in acidic water under visible-light irradiation. A Ru
complex (
) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-
:2',3'-
:3″,2″-
:2‴,3‴-
]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex
itself but the protonated form,
-H
, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate,
-H
was converted to the corresponding dihydro-intermediate (
-H
), where the pyrazine moiety of the ligand received 2e
and 2H
from the substrate.
-H
was facilely oxidized by O
to recover
-H
. Consequently, an oxidation product of the substrate and H
O
derived from dioxygen reduction were obtained; however, the H
O
formed was also used for oxidation of
-H
. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by
-H
was achieved in neither the lowest singlet excited state nor triplet excited state (S
or T
) but in the second lowest singlet excited state (S
), i.e.,
(π-π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by
-H
can be categorized into unusual anti-Kasha photocatalysis. We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e–-oxidized products without the reductive activation of O2 in acidic water under visible-light irradiation. A RuII complex (1) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1-H+, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1-H+ was converted to the corresponding dihydro-intermediate (2-H+), where the pyrazine moiety of the ligand received 2e– and 2H+ from the substrate. 2-H+ was facilely oxidized by O2 to recover 1-H+. Consequently, an oxidation product of the substrate and H2O2 derived from dioxygen reduction were obtained; however, the H2O2 formed was also used for oxidation of 2-H+. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1-H+ was achieved in neither the lowest singlet excited state nor triplet excited state (S1 or T1) but in the second lowest singlet excited state (S2), i.e., 1(π–π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1-H+ can be categorized into unusual anti-Kasha photocatalysis. We have developed photocatalytic oxidation of aromatic substrates using O 2 as a terminal oxidant to afford only 2e – -oxidized products without the reductive activation of O 2 in acidic water under visible-light irradiation. A Ru II complex ( 1 ) bearing a pyrazine moiety as the active site in tetrapyrido[3,2- a :2′,3′- c :3″,2″- h :2‴,3‴- j ]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1 -H + , protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1 -H + was converted to the corresponding dihydro-intermediate ( 2 -H + ), where the pyrazine moiety of the ligand received 2e – and 2H + from the substrate. 2 -H + was facilely oxidized by O 2 to recover 1 -H + . Consequently, an oxidation product of the substrate and H 2 O 2 derived from dioxygen reduction were obtained; however, the H 2 O 2 formed was also used for oxidation of 2 -H + . In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1 -H + was achieved in neither the lowest singlet excited state nor triplet excited state (S 1 or T 1 ) but in the second lowest singlet excited state (S 2 ), i.e., 1 (π–π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1 -H + can be categorized into unusual anti-Kasha photocatalysis. We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e--oxidized products without the reductive activation of O2 in acidic water under visible-light irradiation. A RuII complex (1) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-a:2',3'-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1-H+, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1-H+ was converted to the corresponding dihydro-intermediate (2-H+), where the pyrazine moiety of the ligand received 2e- and 2H+ from the substrate. 2-H+ was facilely oxidized by O2 to recover 1-H+. Consequently, an oxidation product of the substrate and H2O2 derived from dioxygen reduction were obtained; however, the H2O2 formed was also used for oxidation of 2-H+. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1-H+ was achieved in neither the lowest singlet excited state nor triplet excited state (S1 or T1) but in the second lowest singlet excited state (S2), i.e., 1(π-π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1-H+ can be categorized into unusual anti-Kasha photocatalysis.We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e--oxidized products without the reductive activation of O2 in acidic water under visible-light irradiation. A RuII complex (1) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-a:2',3'-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1-H+, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1-H+ was converted to the corresponding dihydro-intermediate (2-H+), where the pyrazine moiety of the ligand received 2e- and 2H+ from the substrate. 2-H+ was facilely oxidized by O2 to recover 1-H+. Consequently, an oxidation product of the substrate and H2O2 derived from dioxygen reduction were obtained; however, the H2O2 formed was also used for oxidation of 2-H+. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1-H+ was achieved in neither the lowest singlet excited state nor triplet excited state (S1 or T1) but in the second lowest singlet excited state (S2), i.e., 1(π-π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1-H+ can be categorized into unusual anti-Kasha photocatalysis. We have developed photocatalytic oxidation of aromatic substrates using O₂ as a terminal oxidant to afford only 2e–-oxidized products without the reductive activation of O₂ in acidic water under visible-light irradiation. A Ruᴵᴵ complex (1) bearing a pyrazine moiety as the active site in tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) as a ligand was employed as a photocatalyst. The active species for the photocatalysis was revealed to be not complex 1 itself but the protonated form, 1-H⁺, protonated at the vacant diimine site of tpphz. Upon photoexcitation in the presence of an organic substrate, 1-H⁺ was converted to the corresponding dihydro-intermediate (2-H⁺), where the pyrazine moiety of the ligand received 2e– and 2H⁺ from the substrate. 2-H⁺ was facilely oxidized by O₂ to recover 1-H⁺. Consequently, an oxidation product of the substrate and H₂O₂ derived from dioxygen reduction were obtained; however, the H₂O₂ formed was also used for oxidation of 2-H⁺. In the oxidation of benzyl alcohol to benzaldehyde, the turnover number reached 240 for 10 h, and the quantum yield was determined to be 4.0%. The absence of ring-opening products in the oxidation of cyclobutanol suggests that the catalytic reaction proceeds through a mechanism involving formal hydride transfer. Mechanistic studies revealed that the photocatalytic substrate oxidation by 1-H⁺ was achieved in neither the lowest singlet excited state nor triplet excited state (S₁ or T₁) but in the second lowest singlet excited state (S₂), i.e., ¹(π–π*)* of the tpphz ligand. Thus, the photocatalytic substrate oxidation by 1-H⁺ can be categorized into unusual anti-Kasha photocatalysis. |
| Author | Fujitsuka, Mamoru Nishi, Taichiro Ishizuka, Tomoya Kotani, Hiroaki Namura, Nanase Osakada, Yasuko Yoshizawa, Kazunari Kojima, Takahiko Shiota, Yoshihito |
| AuthorAffiliation | Institute for Materials Chemistry and Engineering SANKEN (The Institute of Scientific and Industrial Research) Department of Chemistry, Faculty of Pure and Applied Sciences |
| AuthorAffiliation_xml | – sequence: 0 name: Institute for Materials Chemistry and Engineering – sequence: 0 name: Department of Chemistry, Faculty of Pure and Applied Sciences – sequence: 0 name: SANKEN (The Institute of Scientific and Industrial Research) |
| Author_xml | – sequence: 1 givenname: Tomoya orcidid: 0000-0002-3897-026X surname: Ishizuka fullname: Ishizuka, Tomoya organization: Department of Chemistry, Faculty of Pure and Applied Sciences – sequence: 2 givenname: Taichiro surname: Nishi fullname: Nishi, Taichiro organization: Department of Chemistry, Faculty of Pure and Applied Sciences – sequence: 3 givenname: Nanase surname: Namura fullname: Namura, Nanase organization: Department of Chemistry, Faculty of Pure and Applied Sciences – sequence: 4 givenname: Hiroaki orcidid: 0000-0001-7737-026X surname: Kotani fullname: Kotani, Hiroaki organization: Department of Chemistry, Faculty of Pure and Applied Sciences – sequence: 5 givenname: Yasuko orcidid: 0000-0003-4078-0112 surname: Osakada fullname: Osakada, Yasuko organization: SANKEN (The Institute of Scientific and Industrial Research) – sequence: 6 givenname: Mamoru orcidid: 0000-0002-2336-4355 surname: Fujitsuka fullname: Fujitsuka, Mamoru organization: SANKEN (The Institute of Scientific and Industrial Research) – sequence: 7 givenname: Yoshihito orcidid: 0000-0003-2054-9845 surname: Shiota fullname: Shiota, Yoshihito organization: Institute for Materials Chemistry and Engineering – sequence: 8 givenname: Kazunari orcidid: 0000-0002-6279-9722 surname: Yoshizawa fullname: Yoshizawa, Kazunari organization: Institute for Materials Chemistry and Engineering – sequence: 9 givenname: Takahiko orcidid: 0000-0001-9941-8375 surname: Kojima fullname: Kojima, Takahiko email: kojima@chem.tsukuba.ac.jp organization: Department of Chemistry, Faculty of Pure and Applied Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39561282$$D View this record in MEDLINE/PubMed |
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| Snippet | We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e–-oxidized products without the reductive... We have developed photocatalytic oxidation of aromatic substrates using O as a terminal oxidant to afford only 2e -oxidized products without the reductive... We have developed photocatalytic oxidation of aromatic substrates using O2 as a terminal oxidant to afford only 2e--oxidized products without the reductive... We have developed photocatalytic oxidation of aromatic substrates using O₂ as a terminal oxidant to afford only 2e–-oxidized products without the reductive... We have developed photocatalytic oxidation of aromatic substrates using O 2 as a terminal oxidant to afford only 2e – -oxidized products without the reductive... |
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| StartPage | 33022 |
| SubjectTerms | active sites benzaldehyde benzyl alcohol hydrides irradiation ligands light moieties oxidants oxidation oxygen photocatalysis photocatalysts pyrazines ruthenium species |
| Title | Photocatalytic Substrate Oxidation Catalyzed by a Ruthenium(II) Complex with a Phenazine Moiety as the Active Site Using Dioxygen as a Terminal Oxidant |
| URI | http://dx.doi.org/10.1021/jacs.4c09962 https://www.ncbi.nlm.nih.gov/pubmed/39561282 https://www.proquest.com/docview/3130827253 https://www.proquest.com/docview/3154259578 https://pubmed.ncbi.nlm.nih.gov/PMC11622244 |
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