Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377, München, Germany.
Angew Chem Int Ed Engl. 2021 Apr 26;60(18):10409-10414. doi: 10.1002/anie.202101682. Epub 2021 Mar 17.
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 1-type mechanism was proposed and evidenced by experimental studies. 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.
通过无过渡金属、一锅两步法，我们制备了各种功能化三芳基甲烷和 1,1-二芳基链烷衍生物，该方法涉及到各种苯甲醛二乙酸酯与有机锌试剂的反应。通过改变溶剂从四氢呋喃到甲苯，可以实现连续交叉偶联，并且通过实验研究提出并证明了两步 S1 型机理。该方法的合成实用性进一步通过几种具有生物相关性的分子的合成得到了证明，例如抗结核药物、抗乳腺癌药物、神经鞘氨醇-1-磷酸（S1P）受体调节剂的前体和 FLAP 抑制剂。
