The Last Fortress of Tin's Tyranny – Protodenitration of Nitroalkanes

Protodenitration, a direct reduction of nitroalkanes to corresponding alkanes, already spans two centuries and is enabled by various reagents. This mini‐review provides a historical development of the fundamental transformation and highlights the governing position of the Ono‐Tanner reaction employi...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-04, Vol.26 (13), p.n/a
Main Authors: Valachová, Dominika, Marčeková, Michaela, Caletková, Oľga, Kolarovič, Andrej, Jakubec, Pavol
Format: Article
Language:English
Subjects:
Alkanes
Direct reduction
Fortresses
Hydrides
nitroalkane
Ono-Tanner reaction
protodenitration
Reagents
sustainable reduction
Tributyltin compounds
tributyltin hydride
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Summary:Protodenitration, a direct reduction of nitroalkanes to corresponding alkanes, already spans two centuries and is enabled by various reagents. This mini‐review provides a historical development of the fundamental transformation and highlights the governing position of the Ono‐Tanner reaction employing tributyltin hydride. Due to the unchallenged dominance of the toxic tributyltin hydride and environmentally unpopular solvents sharply contrasting with modern ecological trends, the current situation was dubbed “the last fortress of tin's tyranny.” Methods used for the protodenitration of nitroalkanes were reviewed. Despite several decades of intense research, the most frequently used option remains the Ono‐Tanner reaction employing toxic tributyltin hydride. Thus, the protodenitration of nitroalkanes remains the last fortress of the tyranny of tin.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201341