A Solvent-Regulated Dediazotized Oxygenation of α-Aryl α-Diazoesters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

doi:10.6023/cjoc202204057

Abstract

A new metal-free, solvent-regulated dediazotized oxygenation of α-aryl α-diazo esters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is reported. The reaction of α-aryl α-diazo esters and DDQ in 2∶1 molar ratio in dichloromethane (DCM) underwent double dediazotized O—H bond insertion reactions to access α,α'-(1,4- phenyldioxy)diesters as major products, whereas a series of structurally complex α,α-diaryloxy esters were provided with moderate to good yields when the reaction of these substrates in 3∶2 molar ratio in dichloroethane (DCE) proceeded through a double dediazotized O—H bond insertion and dediazotized deoxygenation cascade. The controlled experiments confirmed that the hydrogen atom is from water during O—H bond insertion process. In addition, the reaction featured mild conditions, simple operation and controllable chemoselectivity without any catalyst.

Key words: oxygenation, dediazotization, chemoselectivity, divergent synthesis

Cite this article

Runhong Jia, Shuai Liu, Shichao Wang, Wenjuan Hao, Bo Jiang. A Solvent-Regulated Dediazotized Oxygenation of α-Aryl α-Diazoesters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2814-2822.

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溶剂调控的α-芳基α-重氮酯与2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)的去重氮化氧合反应