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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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 145; no. 36; pp. 19925 - 19931
Main Authors: Xie, Katherine A., Bednarova, Eva, Joe, Candice L., Lin, Chenxi, Sherwood, Trevor C., Simmons, Eric M., Lainhart, Brendan C., Rovis, Tomislav
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 13.09.2023
Subjects:
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
RED
INFRARED LIGHT
IRIDIUM(III) COMPLEXES
GENERATION
RADICALS
PHOTOPHYSICAL PROPERTIES
PHOTOREDOX CATALYSIS
ISSN:0002-7863, 1520-5126, 1520-5126
Online Access:Get more information
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Summary: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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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c06285