DDQ 作为一种多功能且易于回收的氧化剂：系统评价。,RSC Advances

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DDQ 作为一种多功能且易于回收的氧化剂：系统评价。
RSC Advances ( IF 3.9 ) Pub Date : 2021-09-08 , DOI: 10.1039/d1ra04575j
Meshari A Alsharif ₁ , Qandeel Alam Raja ₂ , Nida Abdul Majeed ₂ , Rabab S Jassas ₃ , Abdulrahman A Alsimaree ₄ , Amina Sadiq ₅ , Nafeesa Naeem ₂ , Ehsan Ullah Mughal ₂ , Reem I Alsantali ₆ , Ziad Moussa ₇ , Saleh A Ahmed _{1,

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Affiliation

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 是最广泛使用的具有高还原电位的醌，它通常介导氢化物转移反应并显示出三种可接近的氧化态：醌（氧化）、半醌（单电子还原）和对苯二酚（双电子还原）。DDQ 作为化学计量氧化剂在活化 CH 键的官能化和饱和 CC、CO 和 CN 键的脱氢中具有广泛的用途。DDQ 的成本和毒性引发了最近开发使用催化量 DDQ 与替代化学计量氧化剂的方法的努力。为选择性氧化非空间位阻富电子苄基甲基醚和苄醇建立了好氧催化方法，并有效地扩展到对甲氧基苄基醚的氧化脱保护，以高选择性生成醇。已知 DDQ 和质子酸的组合可将几种芳族供体氧化为相应的阳离子自由基。激发态 DDQ 将苄基、杂芳烃、氟芳烃、苯和烯烃转化为其自由基阳离子形式，并将氯离子和其他阴离子转化为其各自的自由基。这些反应性中间体已用于在有价值的天然产物和有机化合物的合成中生成 CC 和 CX（N、O 或 Cl）键。然而，据我们所知，仍然没有评论文章专门描述 DDQ 在有机合成中的应用。因此，在本次审查中，

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DDQ as a versatile and easily recyclable oxidant: a systematic review.

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is the most widely used quinone with a high reduction potential, and it commonly mediates hydride transfer reactions and shows three accessible oxidation states: quinone (oxidized), semiquinone (one-electron-reduced), and hydroquinone (two-electron-reduced). DDQ has found broad utility as a stoichiometric oxidant in the functionalization of activated C-H bonds and the dehydrogenation of saturated C-C, C-O, and C-N bonds. The cost and toxicity of DDQ triggered recent efforts to develop methods that employ catalytic quantities of DDQ in combination with alternative stoichiometric oxidants. The aerobic catalytic approach was established for the selective oxidation of non-sterically hindered electron-rich benzyl methyl ethers and benzylic alcohols, and effectively extended to the oxidative deprotection of p-methoxybenzyl ethers to generate the alcohols in high selectivity. A combination of DDQ and protic acid is known to oxidize several aromatic donors to the corresponding cation radicals. The excited-state DDQ converts benzyls, heteroarenes, fluoroarenes, benzene, and olefins into their radical cation forms as well as chloride and other anions into their respective radicals. These reactive intermediates have been employed for the generation of C-C and C-X (N, O, or Cl) bonds in the synthesis of valuable natural products and organic compounds. To the best of our knowledge, however, there is still no review article exclusively describing the applications of DDQ in organic synthesis. Therefore, in the present review, we provide an overview of DDQ-induced organic transformations with their scope, limitations and the proposed reaction mechanisms.

更新日期：2021-09-08

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