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

doi:10.6023/cjoc202204057

摘要/Abstract

报道了一类新型无金属、溶剂调控的2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)与α-芳基α-重氮酸酯的去重氮化氧合反应. 当反应使用二氯甲烷作溶剂时, DDQ与α-芳基α-重氮酯以物质的量比1∶2发生双去重氮化氧氢键插入反应, 得到α,α'-(1,4-苯二氧基)二酯衍生物为主要产物, 而使用1,2-二氯乙烷时, 该反应底物以物质的量比2∶3进行反应, 经双去重氮化氧氢键插入和去重氮化双氧合反应串联过程合成了一系列结构复杂的α,α-双芳氧基酯衍生物, 收率中等至良好. 控制实验证实了氧氢插入过程中的氢元素来自于溶剂中的水分子. 此外, 该反应无需金属催化剂, 具有条件温和、操作简便以及化学选择性可控等优点.

关键词: 氧合反应, 去重氮化反应, 化学选择性, 分叉合成

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

引用此文

贾润红, 刘帅, 王世超, 郝文娟, 姜波. 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[J]. 有机化学, 2022, 42(9): 2814-2822.

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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