Mechanistic and Synthetic Studies of Biaryl Birch Reductions

Mechanistic and Synthetic Studies of Biaryl Birch Reductions
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联芳桦还原的机理与合成研究

DOI:
10.1055/s-0042-1751387
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发表时间:
2023
期刊:
Synthesis
影响因子:
--
通讯作者:
Koide, Kazunori
Koide, Kazunori
中科院分区:
--
文献类型:
--
作者:
Koide, Kazunori

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联芳基的Birch还原通常将两种芳烃之一转化为环己-1,4-二烯。在Birch条件下,联芳基比单环芳烃更具反应性。与单环芳烃的还原不同,联芳基还原在二价阴离子中间体质子化之前通过两个连续的电子转移步骤进行。联芳基的还原和随后的烷基化反应在一锅中迅速增加了分子的复杂性,因此已被用于天然产物和药物样分子的合成。1引言2联芳基的Birch还原的物理有机化学3联芳基作为电子转移的介体4溶解联芳基的方法联芳基化合物的金属还原5用亲电试剂阻断联芳基化合物还原中间体6溶解金属介导的联芳基化合物还原反应的合成应用7展望
The Birch reduction of biaryls generally converts one of the two arenes into a cyclohexa-1,4-diene. Biaryls are more reactive than monocyclic arenes under the Birch conditions. Unlike the reduction of monocyclic arenes, biaryl reduction proceeds through two consecutive electron transfer steps before the protonation of the dianion intermediate. The biaryl reductions and subsequent alkylations in one pot rapidly increase the molecular complexity and thus have been used in the synthesis of natural products and drug-like molecules.1 Introduction2 The Physical Organic Chemistry of the Birch Reduction of Biaryls3 Biaryls as the Mediators of Electron Transfer4 Methods for the Dissolving-Metal Reduction of Biaryls5 Intercepting the Biaryl Reduction Intermediates with Electrophiles6 Synthetic Applications of the Dissolving-Metal-Mediated Reductions of Biaryls7 Outlook
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