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<p>This review discusses recent progress in the most significant synthetic approaches involving transformations under the Mitsunobu reaction. The Mitsunobu reaction entails the "redox" condensation of an acidic pronucleophile ‘<i>Nu</i>-H’ and an electrophilic primary or secondary alcohol, facilitated by stoichiometric amounts of phosphines and azodicarboxylate reagents. Widely utilized for dehydrative oxidation–reduction condensation, this reaction shows synthetic utility through its tolerance of a broad range of acidic pronucleophiles, including carboxylic acids, pro-imides, hydroxamates, phenols, thiols, fluorinated alcohols, oximes, thioamides, pyridinium and imidazolium salts, pyrimidine bases, <i>α</i>-ketoesters, and trimethylmethane tricarboxylate, thereby yielding a variety of functional and potentially biologically active compounds. The purpose of this review is to focus on recent advances and applications of Mitsunobu reaction chemistry, particularly from 2010 to 2024. In addition to discussing newer reagents that facilitate purification, we will describe contemporary applications of this chemistry, especially concerning the synthesis of potential biological compounds and their precursors. This focus review of the Mitsunobu reaction summarizes its origins, the current understanding of its mechanism, and recent improvements and applications. We aim for this work to serve as a useful resource for scientists working in this research domain.</p>

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Recent Advances in the Mitsunobu and Related Reactions: A Review from 2010 to 2024

  • 期刊论文

  • 发表日期：

    2025年3月18日

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  • Abdeslem Bouzina,
  • Zineb Aouf,
  • Aϊcha Amira,
  • Yousra Ouafa Bouone,
  • Houria Bentoumi,
  • Yasmine Chemam,
  • Malika Ibrahim-Ouali,
  • Rachida Zerrouki,
  • Nour-Eddine Aouf

摘要

This review discusses recent progress in the most significant synthetic approaches involving transformations under the Mitsunobu reaction. The Mitsunobu reaction entails the "redox" condensation of an acidic pronucleophile ‘Nu-H’ and an electrophilic primary or secondary alcohol, facilitated by stoichiometric amounts of phosphines and azodicarboxylate reagents. Widely utilized for dehydrative oxidation–reduction condensation, this reaction shows synthetic utility through its tolerance of a broad range of acidic pronucleophiles, including carboxylic acids, pro-imides, hydroxamates, phenols, thiols, fluorinated alcohols, oximes, thioamides, pyridinium and imidazolium salts, pyrimidine bases, α-ketoesters, and trimethylmethane tricarboxylate, thereby yielding a variety of functional and potentially biologically active compounds. The purpose of this review is to focus on recent advances and applications of Mitsunobu reaction chemistry, particularly from 2010 to 2024. In addition to discussing newer reagents that facilitate purification, we will describe contemporary applications of this chemistry, especially concerning the synthesis of potential biological compounds and their precursors. This focus review of the Mitsunobu reaction summarizes its origins, the current understanding of its mechanism, and recent improvements and applications. We aim for this work to serve as a useful resource for scientists working in this research domain.