Université Paris-Saclay, CNRS, BioCIS, 92290 Châtenay-Malabry, France.
J Org Chem. 2022 Jan 21;87(2):1249-1261. doi: 10.1021/acs.joc.1c02580. Epub 2022 Jan 11.
This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling -tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consisted of PdCl(CHCN)/dppp, LiOBu as a base, and cyclopentyl methyl ether as a green solvent. In addition, we performed a gram-scale transformation using NTH derivatives and benzylic phosphates having a C sp-Cl bond. The latter was used as a starting point for further postfunctionalization of the key intermediates.
本研究表明，通过将 - 对甲苯磺酰腙（NTHs）与苄基磷酸酯作为亲电试剂偶联，可以高化学选择性地获得高产率的各种二取代和三取代烯烃。所得的新催化体系由 PdCl(CHCN)/dppp、LiOBu 作为碱和环戊基甲基醚作为绿色溶剂组成。此外，我们还使用 NTH 衍生物和具有 C sp-Cl 键的苄基磷酸酯进行了克级转化。后者可作为关键中间体进一步官能化的起点。
