Sulfite-Promoted Synthesis of <i>N</i>-Difluoromethylthioureas via the Reaction of Azoles with Bromodifluoroacetate and Elemental Sulfur

Deng, Jiyong; Gao, Yongchao; Zhu, Zhu; Xu, Lijin; Li, Zhaodong; Tang, Ri‐Yuan

doi:10.1021/acs.orglett.8b03876

Cited by 29 publications

(26 citation statements)

References 44 publications

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“…Quite recently, Tang's group has synthesized N‐ difluoromethylthiourea derivatives 95 using the reaction of azoles 93 with bromodifluoroacetate 94 and rongalite (Scheme ) . In their study, they have tried diverse sulfite reagents for dehalogenation reaction but they observed that rongalite gave better yields in the presence of dimethylacetamide (DMA) solvent at 100 °C.…”

Section: Applications Of Rongalite Chemistry In Organic Synthesismentioning

confidence: 99%

New Dimensions in Rongalite Chemistry: The Land of Opportunities in Organic Synthesis and Material Sciences

Ali

2020

ChemistrySelect

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Rongalite, first time reported in the chemical structure in 1905, also known as bruggolite or sodium formaldehyde sulfoxylate, having good solubility and stability in organic media, is not only a cheap and commercially available (in kg amount) reagent with a range of industrial applications for instance emulsion polymerization, an excellent decolouring agent, antioxidant in pharmaceutical development, and an antidote for heavy metals, but also used as an effective regents in a plethora of organic reactions particularly in redox reactions as a powerful reducing agent. More interestingly, in recent years, it has also shown its impact in material sciences for the preparation of CdTe, CoTe2, and Ag2Se thin films, nanowire networks, hollow nanospheres, copper nanoparticles (Cu‐Nps), CdTe‐quantum dots and so forth. Keeping in mind the importance of this vital reagent in both organic chemistry as well as in material sciences, herein I intended to report the recent developments along with a brief overview of old literature wherever necessary to showcase the utility of this valuable reagent. This particular review article not only covers the applications of this environmentaly benign reagent in organic synthesis but also its usefulness in material sciences in particular nanosciences has been exposed for the first time.

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Section: Applications Of Rongalite Chemistry In Organic Synthesismentioning

confidence: 99%

New Dimensions in Rongalite Chemistry: The Land of Opportunities in Organic Synthesis and Material Sciences

Ali

2020

ChemistrySelect

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“…Tang and Li presented a new methodology for the transformation of azoles into N-difluoromethylated thioureas using elemental sulfur, BrCF 2 CO 2 Et as a CF 2 H source and the sulfite salt HOCH 2 SO 2 Na in DMA at 100 °C (Scheme 23, C). 84 The reaction was compatible with a variety of substituted imidazoles, benzimidazoles and triazoles to furnish the corresponding difluoromethyl thiourea products in yields ranging from 13-88%. The corresponding difluoromethyl selenoureas were prepared in the presence of selenium instead of sulfur under the same reaction conditions.…”

Section: Short Review Syn Thesismentioning

confidence: 92%

Recent Progress on the Synthesis of CF2H-Containing Derivatives

Levi¹,

Amir²,

Gershonov³

et al. 2019

Synthesis

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Recent years have witnessed a growing interest in the development of novel synthetic methods and new reagents for the synthesis of difluoromethylated compounds. Dozens of studies have been published on this topic each year over the past few years. These studies are focused on direct and indirect difluoromethylation of various organic functionalities via nucleophilic-, electrophilic-, radical-, carbene- or metal-mediated mechanisms. The present short review covers the very recent studies, published between mid-2017 and early 2019, on the synthesis of compounds containing a CF2H group. A brief summary of the physicochemical properties and medicinal applications of difluoromethylated compounds is also included.1 Introduction2 Nucleophilic Difluoromethylation2.1 Metal-Mediated Nucleophilic Difluoromethylation2.2 Non-Metal Difluoromethyl Nucleophiles3 Radical Difluoromethylation3.1 Metal-Induced Radical Difluoromethylation3.2 Non-Metal-Induced Radical Difluoromethylation3.3 Electrochemically Induced Radical Difluoromethylation4 Carbene-Based Difluoromethylation4.1 Metal-Induced Carbene Difluoromethylation4.2 Non-Metal-Induced Difluoromethyl Carbenes5 Cross-Coupling Difluoromethylation5.1 Palladium-Catalyzed Difluoromethylation5.2 Nickel-Catalyzed Difluoromethylation5.3 Copper-Mediated Difluoromethylation5.4 Iron-Catalyzed Difluoromethylation5.5 Gold-Mediated Difluoromethylation6 Electrophilic Difluoromethylation7 Other Examples7.1 A Difluoromethyl-Borane Complex7.2 A Tellurium Difluoromethyl Derivative8 Summary

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“…The Tang group reported a unique transformation leading to N-difluoromethylated thioureas from azoles (Scheme 55A). 199 To successfully prepare these products, the authors reacted…”

Section: N-difluoromethylationmentioning

confidence: 99%