Visible-light-mediated facile synthesis of disulfides using reusable TiO<sub>2</sub>/MoS<sub>2</sub> nanocomposite photocatalyst

Liu, Wenjie; Wang, Cancan; Huang, Yibo; Chen, Qun; Wang, Liang; He, Ming‐Yang

doi:10.1080/00397911.2016.1199808

Cited by 16 publications

(8 citation statements)

References 33 publications

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“…[59] Later, the same MoS 2 /TiO 2 nanocomposite was expanded into the visible-light-induced facile synthesis of disulfides by the way of aerobic oxidation of thiols, forming new SÀ S bonds (Scheme 15b). [60] In both cases, visible light was harnessed by MoS 2 and the electron transfer to O 2 was facilitated by TiO 2 , which in turn led to the enhanced results for the formation of CÀ S and SÀ S bonds.…”

Section: Integrating Metal Sulfides With Metal Oxidesmentioning

confidence: 99%

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

2019

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metal sulfides belong to an important subgroup of semiconductor photocatalysts that could promote a variety of valuable redox reactions under mild conditions. One notable merit of metal sulfides is their relatively smaller bandgaps than metal oxides, which in turn make sure that many of them can directly utilize visible light. Historically, the deployment of metal sulfides for visible-light-induced organic transformations took place shortly after the genesis of the research field of heterogeneous photocatalysis. In this review, we primarily focus on recent state-of-the-art advancements of metal sulfide photocatalysis aimed at visible-light-induced selective organic transformations. Interests in this specific branch of photocatalysis have been rekindled due to the new methods for materials synthesis; the pursuit of new mechanisms; or the integration of metal sulfides with metal oxides, metal nanoparticles or other emerging materials. Thus we categorize them into four sections according to the different strategies in developing novel or more efficient organic processes. Binary and ternary metal sulfides, usually associated with new materials synthesis and mechanistic insights, can be used directly for visible-lightinduced organic transformations. This is the basis of other further developments and will be introduced firstly. Next, the cooperation between metal sulfides and metal oxides or metal nanoparticles can be conducive to many photocatalytic systems. These developments will be discussed in the next two ensuing sections. Furthermore, the integration of metal sulfides with recent developed emerging materials such as metalorganic frameworks (MOFs), graphene and graphitic carbon nitride (g-C 3 N 4 ) will be discussed in another section to highlight the importance of merging metal sulfides with these materials. We attempt to keep an impartial panorama of these four distinctive sections even though the phases of development are quite different among sections, leaving plenty of room for the future expansion of this burgeoning area.

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Section: Integrating Metal Sulfides With Metal Oxidesmentioning

confidence: 99%

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

2019

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“…The 1 H NMR yield and quantum yield (Φ) of DPD were estimated to be 52 and 0.37%, respectively, based on the amount of thiophenol used (run 3 in Table ). The photochemical coupling of thiols to afford a disulfide has already been reported, albeit that a photocatalyst that acts as a photochemical radical initiator is required. − To the best of our knowledge, this is the first example of a direct photochemical disulfidation of thiophenol in the absence of any additives. In the presence of CO 2 , the same photoreactivity was observed as under N 2 (Figures a and S6), indicating that thiophenol selectively engages in disulfidation rather than reacting with CO 2 upon photoirradiation.…”

Section: Resultsmentioning

confidence: 92%

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp²)–H Carboxylation with CO₂

et al. 2020

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Exploring new types of photochemical reactions is of great interest in the field of synthetic chemistry. Although excited-state hydrogen detachment (ESHD) represents a promising prospective template for additive-free photochemical reactions, applications of ESHD in a synthetic context remains scarce. Herein, we demonstrate the expansion of this photochemical reaction toward oligomerization, disulfidation, and regioselective C(sp2)–H carboxylation of aromatic alcohols, thiols, and amines. In the absence of any radical initiators in tetrahydrofuran upon irradiation with UV light (λ = 280 or 300 nm) under an atmosphere of N2 or CO2, thiols and catechol afforded disulfides and oligomers, respectively, as main products. Especially, the photochemical disulfidation proceeded highly selectively with the NMR and quantum yields of up to 69 and 0.46%, respectively. In stark contrast, the photolysis of phenylenediamines and aminophenols results in photocarboxylation in the presence of CO2 (1 atm). p-Aminophenol was quantitatively carboxylated by photolysis for 17 h with a quantum yield of 0.45%. Furthermore, the photocarboxylation of phenylenediamines and aminophenols proceeds in a highly selective fashion on the aromatic C(sp2)–H bond next to a functional group, which is directed by the site-selective ESHD of the functional groups for the formation of aminyl and hydroxyl radicals.

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“…Expectedly, no reaction occurred in the presence of anatase TiO 2 (entry 12). Our previously reported MoS 2 –TiO 2 (1:10, molar ratio of Mo to Ti) nanocomposite was also evaluated, , and only 25% yield of 3aa was obtained (entry 13). Moreover, simply adding the three components PANI, g-C 3 N 4 , and TiO 2 (with the same loadings as entry 2) to the reaction mixture led to a poor yield of 3aa (21%, not shown in Table ).…”

Section: Resultsmentioning

confidence: 99%

“…Given the importance of α-chloro aryl ketones, and in continuation of our interest in the design and application of semiconductor photocatalysts, , herein, we report the preparation of a ternary PANI–g-C 3 N 4 –TiO 2 composite and demonstrate its application in the chemoselective synthesis of α-chloro aryl ketones (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed Facile Synthesis of α-Chloro Aryl Ketones with Polyaniline–g-C₃N₄–TiO₂ Composite under Visible Light

Liu

Wang

2017

Ind. Eng. Chem. Res.

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PANI (polyaniline)–g-C3N4–TiO2 composite was prepared and utilized in the photocatalyzed synthesis of α-chloro aryl ketones via a radical-triggered domino process under oxygen atmosphere. This semiconductor photocatalyst showed good photocatalytic performance and chemoselectivity under visible light irradiation. A variety of aryl diazonium salts and aryl alkynes survived the reaction conditions well to afford the corresponding products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. The recycle studies showed that the semiconductor composite could be readily recovered and reused for eight consecutive runs with a slight decrease in the catalytic activity. Control experiments were also performed, and a plausible catalytic mode was proposed.

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Visible-light-mediated facile synthesis of disulfides using reusable TiO₂/MoS₂ nanocomposite photocatalyst

Cited by 16 publications

References 33 publications

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp²)–H Carboxylation with CO₂

Photocatalyzed Facile Synthesis of α-Chloro Aryl Ketones with Polyaniline–g-C₃N₄–TiO₂ Composite under Visible Light

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Visible-light-mediated facile synthesis of disulfides using reusable TiO2/MoS2 nanocomposite photocatalyst

Cited by 16 publications

References 33 publications

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Metal Sulfide Photocatalysis: Visible‐Light‐Induced Organic Transformations

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp2)–H Carboxylation with CO2

Photocatalyzed Facile Synthesis of α-Chloro Aryl Ketones with Polyaniline–g-C3N4–TiO2 Composite under Visible Light

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Visible-light-mediated facile synthesis of disulfides using reusable TiO₂/MoS₂ nanocomposite photocatalyst

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp²)–H Carboxylation with CO₂

Photocatalyzed Facile Synthesis of α-Chloro Aryl Ketones with Polyaniline–g-C₃N₄–TiO₂ Composite under Visible Light