Orange Light-Driven C(sp2)-C(sp3) Cross-Coupling via Spin-Forbidden Ir(III) Metallaphotoredox Catalysis
We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp(2))-C(sp(3)) bonds inacces...
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| Vydané v: | Journal of the American Chemical Society Ročník 145; číslo 36; s. 19925 - 19931 |
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| Hlavní autori: | , , , , , , , |
| Médium: | Journal Article |
| Jazyk: | English |
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WASHINGTON
Amer Chemical Soc
13.09.2023
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| ISSN: | 0002-7863, 1520-5126, 1520-5126 |
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| Abstract | We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp(2))-C(sp(3)) bonds inaccessible with existing methods of low-energy light-driven dual nickel/photoredox catalysis, demonstrating the synthetic utility of this photocatalyst family. The photocatalysts are capable of accessing both oxidatively and reductively activated coupling partners, illustrated through deaminative arylation and potassium alkyl trifluoroborate cross-coupling reactions with aryl halides. We demonstrate diverse substrate scopes of both cross-coupling paradigms under mild conditions in the first example of low-energy light-driven C(sp(2))-C(sp(3)) metallaphotoredox coupling. |
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| AbstractList | We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp(2))-C(sp(3)) bonds inaccessible with existing methods of low-energy light-driven dual nickel/photoredox catalysis, demonstrating the synthetic utility of this photocatalyst family. The photocatalysts are capable of accessing both oxidatively and reductively activated coupling partners, illustrated through deaminative arylation and potassium alkyl trifluoroborate cross-coupling reactions with aryl halides. We demonstrate diverse substrate scopes of both cross-coupling paradigms under mild conditions in the first example of low-energy light-driven C(sp(2))-C(sp(3)) metallaphotoredox coupling. We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp2)-C(sp3) bonds inaccessible with existing methods of low-energy light-driven dual nickel/photoredox catalysis, demonstrating the synthetic utility of this photocatalyst family. The photocatalysts are capable of accessing both oxidatively and reductively activated coupling partners, illustrated through deaminative arylation and potassium alkyl trifluoroborate cross-coupling reactions with aryl halides. We demonstrate diverse substrate scopes of both cross-coupling paradigms under mild conditions in the first example of low-energy light-driven C(sp2)-C(sp3) metallaphotoredox coupling.We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp2)-C(sp3) bonds inaccessible with existing methods of low-energy light-driven dual nickel/photoredox catalysis, demonstrating the synthetic utility of this photocatalyst family. The photocatalysts are capable of accessing both oxidatively and reductively activated coupling partners, illustrated through deaminative arylation and potassium alkyl trifluoroborate cross-coupling reactions with aryl halides. We demonstrate diverse substrate scopes of both cross-coupling paradigms under mild conditions in the first example of low-energy light-driven C(sp2)-C(sp3) metallaphotoredox coupling. |
| Author | Lin, Chenxi Joe, Candice L. Lainhart, Brendan C. Sherwood, Trevor C. Simmons, Eric M. Bednarova, Eva Xie, Katherine A. Rovis, Tomislav |
| Author_xml | – sequence: 1 givenname: Katherine A. surname: Xie fullname: Xie, Katherine A. organization: Columbia Univ, Dept Chem, New York, NY 10027 USA – sequence: 2 givenname: Eva surname: Bednarova fullname: Bednarova, Eva organization: Columbia Univ, Dept Chem, New York, NY 10027 USA – sequence: 3 givenname: Candice L. orcidid: 0000-0002-7167-2416 surname: Joe fullname: Joe, Candice L. organization: Chem Proc Dev, Bristol Myers Squibb, 1 Squibb Dr, New Brunswick, NJ 08903 USA – sequence: 4 givenname: Chenxi surname: Lin fullname: Lin, Chenxi organization: Barnard Coll, Dept Chem, New York, NY 10027 USA – sequence: 5 givenname: Trevor C. orcidid: 0000-0003-3070-6373 surname: Sherwood fullname: Sherwood, Trevor C. organization: Small Mol Drug Discovery, Bristol Myers Squibb, Princeton, NJ 08543 USA – sequence: 6 givenname: Eric M. orcidid: 0000-0002-3854-1561 surname: Simmons fullname: Simmons, Eric M. organization: Chem Proc Dev, Bristol Myers Squibb, 1 Squibb Dr, New Brunswick, NJ 08903 USA – sequence: 7 givenname: Brendan C. surname: Lainhart fullname: Lainhart, Brendan C. organization: Chem Proc Dev, Bristol Myers Squibb, 1 Squibb Dr, New Brunswick, NJ 08903 USA – sequence: 8 givenname: Tomislav orcidid: 0000-0001-6287-8669 surname: Rovis fullname: Rovis, Tomislav email: tr2504@columbia.edu organization: Columbia Univ, Dept Chem, New York, NY 10027 USA |
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| Keywords | RED INFRARED LIGHT IRIDIUM(III) COMPLEXES GENERATION RADICALS PHOTOPHYSICAL PROPERTIES PHOTOREDOX CATALYSIS |
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| Snippet | We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light... |
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| Title | Orange Light-Driven C(sp2)-C(sp3) Cross-Coupling via Spin-Forbidden Ir(III) Metallaphotoredox Catalysis |
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