2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

Introduction

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [1] is a powerful oxidizing agent and has proved to be versatile reagent for various organic transformations. Apart from its well-known applications as a dehydrogenating and oxidizing agent, in recent years it has found number of other applications in synthetic chemistry, including deprotection of various functional groups, cleavage of linker ­molecules from solid support, introduction of unsaturation and C-C, C-O and C-N bond-formation reactions. In recent years, it has shown wide potential for oxidative ­cyclization leading to a variety of heterocyclic ring skeletons such as benzopyrans, xanthenes, alkylindans, benz­oxazoles, and oxazolidinones. It has found application in steroid chemistry and in the synthesis of complex natural products, [2] where its unique regioselective properties gave excellent results for the preparation of key intermediates. DDQ was also found to be an excellent reagent to cleave methoxybenzyl ethers [3] and an efficient catalyst for the ­alcoholysis of epoxides [4] as well as for the hydrolysis of acetals. [5]

DDQ is commercially available and its first synthesis was described by Thiele and Gunther in 1906. It can be ­prepared by a six-step procedure involving cyanation and chlorination of benzoquinone. [6]

References

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