Visible-Light-Promoted, Catalyst-Free Gomberg–Bachmann Reaction: Synthesis of Biaryls

Lee, Juyoung; Hong, Boseok; Lee, Anna

doi:10.1021/acs.joc.9b00557

Cited by 37 publications

(29 citation statements)

References 90 publications

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“…22,23 A variety of sacricial donor compounds have been used in the literature such as N,N-dimethylaniline, 24 triethylamine, 25 1,3,5trimethoxybenzene (TMB), 26 and pyridine. 27 Thus, the photoarylation of pyrazine hydrochloride (1b) with p-methoxybenzenediazonium tetrauoroborate (2a) was carried out using TMB or pyridine as sacricial donors. However, product 3a was obtained in 28 and 33% yields, respectively (Table 1, entries 15 and 16).…”

Section: Resultsmentioning

confidence: 99%

Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light

et al. 2020

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Section: Resultsmentioning

confidence: 99%

Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light

et al. 2020

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“…discovered a metal‐/photosensitizer‐free visible light‐induced Gomberg‐Bachmann reaction for the synthesis of biaryls under mild reaction conditions (Scheme 22). [87] Various aryl diazonium salts were well tolerated in this reaction system. The generation of an EDA complex between aryl diazonium salts and pyridine promotes the formation of biaryls under visible light irradiation in moderate to high yields.…”

Section: Photoinduced Radical Addition Reactions Promoted By Eda Complexesmentioning

confidence: 97%

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

et al. 2021

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Photocatalyzed organic synthesis transformation is a remarkable green synthetic strategy because of the advantages of operational simplicity, high chemoselectivities, cheap, and environmental benignancy, along with the extensive applications in the fields of organic, pharmaceutical and functional material chemistry. Generally, photoredox catalysts or photosensitizers are necessary for the generation of their excited states to perform the successive oxidative or reductive reactions through the single electron transfer (SET) or energy transfer (ET) process. Furthermore, the exploration of a colored electron donor-acceptor (EDA) complex or a charge transfer (CT) complex between an electron-rich and an electron-poor substrate provides the chance to deliver the excited intermediate under the irradiation of light, resulting in the formation of radical activate species through a single electron transfer to induce successive various radical reactions. These reactions were performed without the need of any external photocatalysts under mild reaction conditions. Herein, this review focuses on the recent progress on photoinduced radical addition reactions, radical borylations, reductive reactions, radical-radical cross-coupling reactions, degradation reactions and radical cascade cyclization via EDA complexes. We highlight these novel green synthetic methodologies and applications, as well as the mechanisms. This review will help to provide references for organic and medicinal chemists who are charmed by these green organic photochemical transformations based on EDA complexes.

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“…zenes and halogenated arenediazonium tetrafluoroborates. 59 The optimized reaction conditions involved the use of the arene as the reactant and solvent in the presence of pyridine under white (430-660 nm), blue (455 nm), or green (530 nm) LED irradiation at room temperature (Table 14). In the case of solid halobenzenes the authors employed DMSO as the solvent, however, they experienced a drop in the reaction yields.…”

Section: Review Synthesismentioning

confidence: 99%

“…Proposed initiation step for the visible-light-promoted Gomberg-Bachmann reaction in the presence of pyridine 59 The EDA complex then undergoes fragmentation under visible-light irradiation, generating the aryl radical that initiates the propagation step, as summarized in Scheme 2.…”

Section: Figure 16mentioning

confidence: 99%

Real Metal-Free C–H Arylation of (Hetero)arenes: The Radical Way

Bellina¹

2021

Synthesis

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Synthetic methodologies involving the formation of carbon-carbon bonds from carbon-hydrogen bonds are of significant synthetic interest, both for efficiency in terms of atom economy and for their undeniable usefulness in late-stage functionalization approaches. Combining these aspects with being metal-free, the radical C-H intermolecular arylation procedures covered by this review represent a powerful green means for the synthesis of (hetero)biaryl systems. 1. Introduction 2. Arylation with arenediazonium salts and related derivatives 2.1. Ascorbic acid as reductant 2.2. Hydrazines as reductants 2.3. Gallic acid as reductant 2.4. Polyanilines as reductants 2.5. Chlorpromazine hydrochloride as reductant 2.6 Phenalenyl-based radicals as reductants 2.7 Electrolytic reduction of diazonium salts 2.8 Visible-light mediated arylation 3. Arylation with arylhydrazines: generation of aryl radicals using an oxidant 4. Arylation with diaryliodonium salts 5. Arylation with aryl halides 6. Conclusions

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Visible-Light-Promoted, Catalyst-Free Gomberg–Bachmann Reaction: Synthesis of Biaryls

Cited by 37 publications

References 90 publications

Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light

Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

Real Metal-Free C–H Arylation of (Hetero)arenes: The Radical Way

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