Aryldiazonium Salts Serve as a Dual Synthon: Construction of Fully Substituted Pyrazoles via Rongalite-Mediated Three-Component Radical Annulation Reaction

Wang, Miao; Tang, Bo‐Cheng; Xiang, Jia‐Chen; Chen, Xianglong; Ma, Jin‐Tian; Wu, Yan‐Dong

doi:10.1021/acs.orglett.9b03212

Cited by 47 publications

(24 citation statements)

References 58 publications

(18 reference statements)

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“…A novel rongalite‐mediated three‐component radical annulation protocol for the synthesis of fully substituted pyrazoles from aryldiazonium tetrafluoroborates and α , β ‐unsaturated aldehydes or ketones was disclosed by Wu and co‐workers (Scheme 10). [20] This synthetic method provides a simple and straightforward approach to construct diverse pyrazole derivatives with a wide substance scope under metal‐ and oxidant‐free conditions. In this transformation, the aryldiazonium salts serve as dual synthons to participate in the tandem radical cyclization reactions, acting as the precursors of both the aryl radicals and aryl hydrazine units.…”

Section: Synthesis Of Pyrazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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Nitrogen heterocycles are important structural subunits that occur widely in bioactive natural products, pharmaceuticals, agrochemicals, dyes, cosmetics, and functional materials. Considering the importance of these useful compounds in modern science, the synthesis of N-heterocycles and their derivatives has always been a hot topic in organic synthesis. Recently, arenediazonium salts which can be easily prepared from inexpensive and abundantly available anilines, have been used as versatile nitrogen sources in the field of nitrogen heterocycle synthetic chemistry due to their ready availability, rich reactivity, and diverse transformations. The aim of the present review is to summarize the recent advances in the synthesis of nitrogen heterocycles using arenediazonium salts as nitrogen sources in the past ten years. Hopefully, it can provide practical guidance for the readers who are interested in utilizing arenediazonium salts as building blocks in organic synthesis. For simplicity and clarity, the organization of this review is based on the number of N atoms in the ring of nitrogen heterocycle.

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Section: Synthesis Of Pyrazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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“…In this context, a one‐pot procedure for the synthesis of fully substituted pyrazoles 9 from α , β ‐unsaturated carbonyl compounds 7 and aryldiazonium salts 6 and 8 has been reported by Wang et al . by virtue of rongalite and triggered by three‐component radical annulation method where rongalite act as a reducing agent as well as radical initiator in contrast aryldiazonium salts helped as a precursor of both the aryl as well as aryl hydrazine subunits (Scheme ) . As can be pointed out from the Scheme , they have assembled diverse pyrazole derivatives 9 by employing this powerful methodology in respectable yields in the presence of rongalite and DMSO at room temperature.…”

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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“…Another general reaction of aryl diazonium salts to construct fully substituted pyrazoles 85 was reported by Wu and co‐workers in 2019 (Scheme 22). [ 131 ] In this rongalite‐promoted formal three‐component transformation, the aryl diazonium salts 30 not only successfully served as aryl hydrazine equivalent to cyclize…”

Section: Cyclization and Cycloaddition Reactions For The Constructionmentioning

confidence: 99%

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

et al. 2020

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Aryl diazonium salts occupy a privileged role in synthetic chemistry owing to their ready availability and versatile reactivity. While their applications in accessing diversely functionalized arene derivatives via denitrogenation‐coupling and reduction/addition reactions have been well recognized by practitioners in both academia and industry, recent renaissance in chemical transformations of retaining the key N2‐unit has emerged as a powerful technique to construct various N‐heterocycles. This review covers the history and latest advances in cyclization and cycloaddition reactions using aryl diazonium salts as N2‐annulation synthons. The scope, applications, and opportunities in exploring new chemical space by this sustainable strategy are summarized and discussed.

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Aryldiazonium Salts Serve as a Dual Synthon: Construction of Fully Substituted Pyrazoles via Rongalite-Mediated Three-Component Radical Annulation Reaction

Cited by 47 publications

References 58 publications

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

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

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

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