Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

Abstract

We have successfully demonstrated an efficient and practical Pd-catalyzed reaction between aziridine and isocyanide, leading to the synthesis of isoindoline derivatives in moderate to good yields. This reaction is particularly noteworthy with readily available starting materials, and the high-tension aziridine is exploited as a nucleophile, a relatively unexplored strategy in the field. The regioselectivity and Z-type stereoselectivity of the final products may be attributed to the presence of intramolecular hydrogen bonds. To substantiate our findings, we have employed single crystal X-ray diffraction and performed DFT calculations, which provide theoretical support for our reported results.