Mitsunobu reaction

Common card · No. 364454

The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). Although DEAD and DIAD are most commonly used, there are a variety of other azodicarboxylates available which facilitate an easier workup and/or purification and in some cases, facilitate the use of more basic nucleophiles. It was discovered by Oyo Mitsunobu (1934–2003). In a typical procedure, the alcohol, carboxylic acid, and triphenylphosphine are dissolved in tetrahydrofuran or other suitable solvent (e.g. diethyl ether), cooled to 0 °C using an ice-bath, a THF solution of the azodicarboxylate is then added slowly, and the reaction stirred at room temperature for several hours. The alcohol reacts with the phosphine to create a good leaving group then undergoes an inversion of stereochemistry in classic SN2 fashion as the nucleophile...

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