Palladium / Xu Phos catalyzed asymmetric tandem heck / Suzuki coupling of o-iodoaryl allylic compounds with organic boric acid

Recently, Zhang Junliang's research group of Fudan University has realized palladium catalyzed tandem heck / Suzuki coupling reaction between o-iodoaryl allylic compounds and organic boric acid with high enantioselectivity by using their independently developed sadphos series ligands (Xu Phos) Relevant work was published in angew Chem Int ed (DOI: 10.1002 / anie 201907840) under the title of "energetic dicarborfunctionalization of inactive alkenes by palladium catalyzed tandem heck / Suzuki coupling reaction" Benzo ring compounds (dihydrofuran, dihydroindole, chroman, dihydroindene, etc.) exist widely in some bioactive molecules Tandem heck like olefin double carbonization is one of the very simple and efficient methods to construct this kind of compounds Starting from a simple and easily available olefin material, two carbon carbon bonds with the same or different carbon bonds can be formed in one step, which shows the strong synthesis potential of this method Therefore, it has attracted extensive attention of chemists It is worth mentioning that at present, this method is mainly limited to racemic synthesis, and its asymmetric synthesis still faces great challenges Therefore, it is of great significance to solve the problem of asymmetric catalysis for the asymmetric synthesis of benzo ring compounds On the basis of its previous work, the palladium catalyzed series heck / Suzuki coupling reaction between o-iodoaryallylic compounds and organic boric acid was carried out to construct benzo cyclic compounds with one chiral quaternary carbon center This method has a very good universality In this system, aryl, alkenyl, alkyl and complex boric acid reagents can be efficiently converted into target products In addition, a pair of enantiomers can be synthesized with high corresponding selectivity by using the same chiral catalyst The first author is Zhang Zhanming, a postdoctoral researcher of Fudan University, and the corresponding author is Professor Zhang Junliang of Fudan University.