Youtor
Staudinger Reaction
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The Staudinger Reaction allows the transformation of organic azides into the corresponding aza-ylides by the reaction with triphenylphosphine. • Reaction mechanism: • 1. Triphenylphosphine reacts with the azide to generate a phosphazide. 2. Next, the phosphazide goes through a four-membered transition state, which upon losing dinitrogen affords the iminophosphorane. 3. Aqueous work up leads to the amine and the very stable phosphine oxide. • References: • NROChemistry: https://nrochemistry.com/staudinger-r... • Example #1: J. Am. Chem. Soc. 2021, 143, 2699. https://doi.org/10.1021/jacs.1c00047 • Example # 2: J. Am. Chem. Soc. 2020, 142, 16039. https://doi.org/10.1021/jacs.0c07433
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