Abstract
Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.
Highlights
The 12 Principles of Green Chemistry, introduced by Anastas and Warner at the end of the 1990s, set guidelines for the development of sustainable and environmentally friendly chemical processes, aiming to reduce and/or eliminate the chemical pollution by improving design, instead of residue treatment
Oxone has been widely used as a green oxidant in organic transformations, generating the nontoxic KHSO4 as the oxidant-derived byproduct
This review highlights the recent advances in the Oxone-mediated synthesis of heterocyclic compounds, bringing mechanistic insights, protocol particularities, and a comprehensive discussion about scope and limitations
Summary
The 12 Principles of Green Chemistry, introduced by Anastas and Warner at the end of the 1990s, set guidelines for the development of sustainable and environmentally friendly chemical processes, aiming to reduce and/or eliminate the chemical pollution by improving design, instead of residue treatment. Principle #12 (Inherently Safer Chemistry for Accident Prevention) is very important, once it encourages the use of safe substrates and reaction conditions, as well as seeking to eliminate the generation of hazardous substances, reducing the risk of accidents involving explosions, leaks and fires [1,2,3] To satisfy this premise, the development of selective protocols, employing green oxidant species and circumventing the use of hazardous oxidants (e.g.,: KMnO4, K2Cr2O7, CrO3, OsO4, tBuOCl, m-CPBA, NBS), are welcome. Oxone has been widely used as a green oxidant in organic transformations, generating the nontoxic KHSO4 as the oxidant-derived byproduct It is a very safe species, presenting an impressive bench-stability, which makes its transportation and storage not dangerous [6].
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