Visible-Light Photoredox-Catalyzed Iminyl Radical Formation by N–H Cleavage with Hydrogen Release and Its Application in Synthesis of Isoquinolines

Tian, Wan‐Fa; Wang, Dangpo; Wang, Shaofeng; He, Ke‐Han; Cao, Xiao‐Ping; Li, Yang

doi:10.1021/acs.orglett.8b00193

Cited by 41 publications

(20 citation statements)

References 69 publications

(20 reference statements)

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“…In 2018, Li and co-workers devised a synthesis of 2-substituted isoquinolines via the dehydrogenative annulative coupling of diaryl NH -ketimines and diaryl alkynes, through a dual photoredox/Co(III) catalytic reaction manifold ( Scheme 97 ). 306 A novel cobaloxime complex bearing a 4- N,N -dimethylamidopyridine (4-Me 2 NCOPy) axial ligand [Co(dmgH) 2 (4-Me 2 NCOPy)Cl] was identified as being highly efficient for hydrogen evolution in this system. Blue-light irradiation of CH 2 Cl 2 solutions of aryl ketimine and aryl alkyne substrates in the presence of the organic photocatalyst N -Me Mes-Acr + ClO 4 – ([ Acr-1 ]ClO 4 ) and this Co(III) complex under a nitrogen atmosphere proved optimal for this transformation.…”

Section: N -Centered Radical Generation From N–h Bonds Through Photochemical and Electrochemical Pcet Processesmentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner’s guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N–H, O–H, S–H, and C–H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X=Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

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Section: N -Centered Radical Generation From N–h Bonds Through Photochemical and Electrochemical Pcet Processesmentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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“…Illustrative example for the photocatalytic oxidative generation of iminyl radicals via an N-H bond oxidation: the radical cyclization reported by Li and co-workers[145].…”

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confidence: 99%

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Amos¹,

Garreau²,

Buzzetti³

et al. 2020

Beilstein J. Org. Chem.

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Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy fine-tuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this review, we provide an overview of the available approaches to access reactive intermediates that employ organophotocatalysis. Our contribution is not a comprehensive description of the work in the area but rather focuses on key concepts, accompanied by a few selected illustrative examples. The review is organized along the type of reactive intermediates formed in the reaction, including C(sp3) and C(sp 2 ) carbon-, nitrogen-, oxygen-, and sulfur-centered radicals, open-shell charged species, and sensitized organic compounds.

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“…This aromatization is facilitated by the simultaneous formation of cobalt hydride, whose protonation results in the release of hydrogen gas and the regeneration of the cobaloxime catalyst. Consecutive formations of C-C and C-N bonds were also demonstrated in the similar reaction design for the preparation of 3,4-dihydroisoquinoline derivatives [60] or isoquinoline derivatives [61].…”

Section: Cchementioning

confidence: 58%

The Merger of Photoredox and Cobalt Catalysis

Kojima

Matsunaga

2020

Trends in Chemistry

127

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Visible-Light Photoredox-Catalyzed Iminyl Radical Formation by N–H Cleavage with Hydrogen Release and Its Application in Synthesis of Isoquinolines

Cited by 41 publications

References 69 publications

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

The Merger of Photoredox and Cobalt Catalysis

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