Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides

Liu, Na; Chao, Fei; Liu, Mingguo; Huang, Nianyu; Zou, Kun; Wang, Long

doi:10.1021/acs.joc.8b03242

Cited by 66 publications

(25 citation statements)

References 43 publications

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“…Later, Wang and co‐workers introduced a direct disulfide‐directed C─H activation for the synthesis of thiophenols from disulfide and arylboronic acid with oxygen as the oxidant . However, none of the previous methods for 2‐(phenylthio)phenol derivatives synthesis could achieve recycling of the catalyst . From the perspectives of sustainable development and easy recovery, it is clearly necessary to develop a recoverable catalytic system to realize the synthesis of 2‐(phenylthio)phenol derivatives with good efficiency and recyclability.…”

Section: Introductionmentioning

confidence: 99%

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Zhang

Wang

et al. 2020

J of Chemical Tech & Biotech

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BACKGROUND Aromatic thioether derivatives exist widely in natural products and have significant applications in modern synthesis and the pharmaceutical industry; for example, 2‐sulfanylphenols and arylthioquinones are important intermediates in the processing of anticancer, antibiotic, antivirus and antimalarial drugs. Direct C─H hydroxylation was considered as one of the efficient methods for the synthesis of these compounds. Homogeneous transition metal catalysts usually were used through a cross‐coupling of halogen‐substituted phenols with thiophenols. However, from the perspectives of sustainable development and easy recovery, it is necessary to develop an efficient and recoverable catalytic system to realize the synthesis of aromatic thioether derivatives with good efficiency and recyclability. RESULTS The heterogeneous catalyst [Cu(binap)I]2@HT in the present work showed good catalytic activity for the C─H hydroxylation of benzenethiol and phenylboronic acid. The catalytic system was tolerant to various substituents including alkyl, alkoxy, ester, halogen or trifluoromethyl on the phenyl ring of the thiophenols or arylboric acids. In addition to electron‐donating groups, the products with strong electron‐withdrawing groups, such as methyl formylate and trifluoromethyl also were achieved with good yields at 90 °C for 12 h (68% and 66%, respectively). Repeated experiment results showed that the catalyst could be reused at least five times without obvious decrease in catalytic activity. CONCLUSION A BINAP‐Cu complex supported on hydrotalcite was prepared and used as a heterogeneous catalyst for the C─H activation of thiophenol under mild reaction conditions. Through a cascade C─H hydroxylation and further oxidation process, 2‐Sulfanylphenols and arylthioquinones could be obtained with moderate‐to‐good yields for a series of 2‐(phenylthio)phenol derivatives using the heterogeneous catalyst [Cu(binap)I]2@HT. In addition, this heterogeneous catalyst showed good recylbility. © 2020 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Zhang

Wang

et al. 2020

J of Chemical Tech & Biotech

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“…Later, researchers found that OMS-2 also demonstrated an excellent performance in the field of organic synthetic catalysis when different metal ions were used to modify OMS. Reflux, [15][16][17][18] ball milling, 19 impregnation, 20 and multi-step hydrothermal methods [21][22][23] can produce OMS doped with Cu.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of diaryl sulfides based on copper-doped OMS-2

Liu

et al. 2020

Journal of Chemical Research

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We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.

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“…Small organic fluorophores are indispensible tools for the construction of fluorescent probes because of the controllable optical properties such as bodipy, coumarin, rhodamine, fluorescein, etc . Among them, fluorophores derived from benzothiazole are widely used as the dye platform for designing of fluorescent probes .…”

Section: Introductionmentioning

confidence: 99%

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

et al. 2019

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A new Light‐Up fluorescent probe (FA‐P) for detection of formaldehyde was designed and synthesized based on the donor‐excited photo induced electron transfer (d‐PeT) process. The probe FA‐P was constructed by integrating a benzothiazole derivatives as the fluorescent skeleton and homoallylamino group as the specific recognition site. It showed the unique advantages of easy‐preparation, and excellent selectivity response toward formaldehyde. Besides, The probe FA‐P can not only detect formaldehyde gas through the prepared test paper, but also detect formaldehyde in serum solution.

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Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides

Cited by 66 publications

References 43 publications

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Synthesis of diaryl sulfides based on copper-doped OMS-2

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

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