Synthetically useful carbon–carbon and carbon–sulphur bond construction mediated by carbon- and sulphur-centred radicals in water and aqueous media

Postigo, Al

doi:10.1039/c1ra00372k

Cited by 30 publications

(4 citation statements)

References 82 publications

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“…Despite these findings, the percentage of synthetic organic radical reactions carried out in the presence of water remained very small [15][16][17] until Macmillan and coworkers introduced the concept of photoredox catalysis [18]. In this review, we will present a variety of radical reactions where water exerts significant influence on the outcome.…”

Section: Organic Reactions In Aqueous Mediamentioning

confidence: 99%

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Chatgilialoglu,

Barata-Vallejo,

Gimisis

2024

Molecules

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Radical reactions in water or aqueous media are important for organic synthesis, realizing high-yielding processes under non-toxic and environmentally friendly conditions. This overview includes (i) a general introduction to organic chemistry in water and aqueous media, (ii) synthetic approaches in, on, and with water as well as in heterogeneous phases, (iii) reactions of carbon-centered radicals with water (or deuterium oxide) activated through coordination with various Lewis acids, (iv) photocatalysis in water and aqueous media, and (v) synthetic applications bioinspired by naturally occurring processes. A wide range of chemical processes and synthetic strategies under different experimental conditions have been reviewed that lead to important functional group translocation and transformation reactions, leading to the preparation of complex molecules. These results reveal how water as a solvent/medium/reagent in radical chemistry has matured over the last two decades, with further discoveries anticipated in the near future.

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Section: Organic Reactions In Aqueous Mediamentioning

confidence: 99%

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Chatgilialoglu,

Barata-Vallejo,

Gimisis

2024

Molecules

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“…Sulfur-centered radicals have been broadly utilized in a wide range of synthetic applications over the past three decades. While their general utility has been previously reviewed [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ], this account seeks to update the reader specifically on the application of thiyl radicals (RS • ), in the carbocyclizations of unsaturated moieties, and the scope and limitations of these reactions in natural product synthesis.…”

Section: Introductionmentioning

confidence: 99%

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

Lynch

Scanlan

2020

Molecules

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Sulfur centered radicals are widely employed in chemical synthesis, in particular for alkene and alkyne hydrothiolation towards thioether bioconjugates. The steadfast radical chain process that enables efficient hydrothiolation has been explored in the context of cascade reactions to furnish complex molecular architectures. The use of thiyl radicals offers a much cheaper and less toxic alternative to the archetypal organotin-based radical methods. This review outlines the development of thiyl radicals as reactive intermediates for initiating carbocyclization cascades. Key developments in cascade cyclization methodology are presented and applications for natural product synthesis are discussed. The review provides a chronological account of the field, beginning in the early seventies up to very recent examples; a span of almost 50 years.

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“…Recently, many aqueous‐phase studies have been reported . Water, as the safest reaction medium, is cheap and widely distributed on the Earth, and possesses significant advantages of mild reaction conditions, anti‐vice, non‐polluting to the environment and effectively preventing loss of product, due to its low solubility of organic products compared with organic solvents.…”

Section: Introductionmentioning

confidence: 99%

A green and efficient method for synthesis of benzimidazoles using nano‐Fe₃O₄ in PEG‐400/H₂O aqueous system under ambient conditions at room temperature

Wang

Zhu

et al. 2014

Applied Organom Chemis

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In this paper, a green and facile protocol was described which was efficient for synthesis of benzimidazoles using nano‐Fe3O4 catalyst with continuous bubbling of air as the oxidant in PEG‐400/H2O aqueous system at room temperature. This protocol afforded the target products in good to excellent yields and the catalytic system could be recycled and reused without significant loss of catalytic activity. Copyright © 2014 John Wiley & Sons, Ltd.

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Synthetically useful carbon–carbon and carbon–sulphur bond construction mediated by carbon- and sulphur-centred radicals in water and aqueous media

Cited by 30 publications

References 82 publications

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

A green and efficient method for synthesis of benzimidazoles using nano‐Fe₃O₄ in PEG‐400/H₂O aqueous system under ambient conditions at room temperature

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Synthetically useful carbon–carbon and carbon–sulphur bond construction mediated by carbon- and sulphur-centred radicals in water and aqueous media

Cited by 30 publications

References 82 publications

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

A green and efficient method for synthesis of benzimidazoles using nano‐Fe3O4 in PEG‐400/H2O aqueous system under ambient conditions at room temperature

Contact Info

Product

Resources

About

A green and efficient method for synthesis of benzimidazoles using nano‐Fe₃O₄ in PEG‐400/H₂O aqueous system under ambient conditions at room temperature