德国慕尼黑大学Paul Knochel团队揭示了无过渡金属苯并二乙酸酯与有机锌试剂顺序交叉偶联合成多官能团三芳基甲烷和1,1-二芳基烷烃策略。 相关研究成果发表在2021年2月24日出版的《德国应用化学》。

通过无过渡金属单罐两步法制备了多官能团三芳基甲烷和1,1-二芳基烷烃衍生物，包括各种苯并二乙酸酯与有机锌试剂的反应。通过将溶剂从THF转化为甲苯，实现了顺序交叉偶联，并通过实验研究提出和证明了两步SN1型机理。

该方法的合成用途还可以通过合成几种生物相关分子来进一步证明，如抗结核药物、抗乳腺癌药物、鞘氨醇- 1 -磷酸(S1P)受体调节剂前体和皮瓣抑制剂。

附：英文原文

Title: Transition Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents

Author: Baosheng Wei, Qianyi Ren, Thomas Bein, Paul Knochel

Issue&Volume: 2021-02-24

Abstract: A variety of functionalized triarylmethane and 1,1‐diarylalkane derivatives were prepared via a transition metal‐free, one‐pot and two‐step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross‐coupling is enabled by changing the solvent from THF to toluene, and a two‐step S  N  1‐type mechanism was proposed and evidenced by experimental study. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti‐tuberculosis agent, an anti‐breast cancer agent, a precursor of a sphingosine‐1‐phosphate (S1P) receptor modulator, and a FLAP inhibitor.

DOI: 10.1002/anie.202101682

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202101682