Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp<sup>2</sup>)–P Formation: Metal-Free C–H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

Luo, Kai; Chen, Yaozhong; Yang, Wenchao; Zhu, Jie; Wu, Lei

doi:10.1021/acs.orglett.5b03497

Cited by 152 publications

(48 citation statements)

References 64 publications

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“…In addition to the transition metal‐catalyzed version, the radical phosphorylation of benzothiazoles has been also achieved through visible light photocatalysis by the groups of Wu and Lei, respectively.…”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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“…by Wu and co‐workers for the phosphorylation of 8‐hydroxyquinolines or 8‐aminoquinolines and by Hong and co‐workers for the phosphinylation of coumarins . Finally, Wu and co‐workers developed a method for the C–H phosphinylation of thiazoles …”

Section: C–p Bondmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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Visible‐light‐mediated chemical reactions have become very popular within the last 15 years. Many excellent reviews have summarized reaction principles and recent results in photochemistry and photocatalysis. However, despite their popularity photochemistry and photoredox catalysis are not regular parts of the bachelor and master curriculum of chemistry education. As a consequence, most chemists will use in synthesis planning classic retrosynthetic disconnections and only rarely consider photocatalytic steps. The aim of this article is to be a useful tool for synthetic chemists, that are interested in the synthetic aspects of photocatalysis and looking for a specific retrosynthetic disconnection. Not only are informative schemes provided but also are the availability of the catalysts and reagents as well as the functional group tolerance of the respective method briefly discussed.

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“…The first direct C−H phosphorylation of thiazole derivatives by organic dye sensitized photocatalysis was disclosed by Wu's group in 2016 . The diarylphosphine oxides and thiazole derivatives underwent a cross‐coupling hydrogen evolution (CCHE) reaction in the presence of a catalytic amount of eosin B and an 11 W white LED.…”

Section: Photocatalytic Synthesis Of Phosphorus‐containing Compoundsmentioning

confidence: 99%

Photoredox Catalysis in Organophosphorus Chemistry

2017

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The vernal blooming of green chemistry has contributed to the development of visible light catalysis. Active radical species are generatedf rom catalytic amounts of photosensitizers,such as transition-metal complexes and organic dyes, upon visible light irradiation. Stoichiometrica mounts of oxidants, reductants, and radical initiators are avoidedi n most cases. Thus, reactions proceed under milder conditions with ab roader functional group tolerance than found by other methods. Photoredoxc atalysis has been used to form CÀCa nd CÀX( X= O, N, and S) bonds but is comparably underdeveloped in organophosphorus chemistry.H erein, we summarize advances in photoredox catalysis that involve organophosphorus chemistry.T he synthesis of organophosphorusc ompounds by photoredox catalysis, transition-metal complex/photoredoxd ual catalytic systems, andp hotoredox catalysis with phosphorus organocatalysts are discussed. The shortcomings and possible future trendso ft his chemistry are also presented.Scheme1.Various photocatalysts for the cross-couplingr eactionso ftetrahydroisoquinoline with dialkylphophonates and diaryl phosphine oxides[ ppy = 2phenylpyridine, bpy = 2,2'-bipyridine, DMF = N,N-dimethylformamide, AIBN = azobis(isobutyronitrile), PVA = poly(vinyl alcohol), BTF = benzotrifluoride].Scheme3.Thiophosphite-mediated RATC process to form five-membered ring and C sp 3 ÀPb ond.Scheme2.The mechanism for the photocatalyzed cross-coupling reaction [PC = Ir complex, Au complex, eosin Y, or rose bengal)].Scheme9.Direct CÀHp hosphorylationoft hiazoles in cross-coupling hydrogen evolution reaction and the proposed mechanism.Scheme11. Hetero-cross-dehydrogenative-coupling reaction of benzothiazoles and H-phosphonates.Scheme10. Hetero-cross-dehydrogenative-coupling reaction of dialkylphosphiteswith N-protected indole and the tentative reaction mechanism.

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Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp²)–P Formation: Metal-Free C–H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

Cited by 152 publications

References 64 publications

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

A Retrosynthetic Approach for Photocatalysis

Photoredox Catalysis in Organophosphorus Chemistry

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Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp2)–P Formation: Metal-Free C–H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

Cited by 152 publications

References 64 publications

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

A Retrosynthetic Approach for Photocatalysis

Photoredox Catalysis in Organophosphorus Chemistry

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Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp²)–P Formation: Metal-Free C–H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides