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.
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.”
Wiley: European Journal of Organic Chemistry: Table of Contents
Authors: Dominika Valachová, Michaela Marčeková, Oľga Caletková, Andrej Kolarovič, Pavol Jakubec