Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles

Abstract

N1-substituted 1,2,4-triazoles are ubiquitous skeletons in medicinal agents, agrochemicals, and organic materials. Herein, an efficient and practical method for the synthesis of N1-allylated 1,2,4-triazoles via Pd-catalyzed allylic substitution of vinylethylene...

Synergistic Organoboron/Palladium Cocatalyzed Dehydrative Couplings of Azoles with Allylic Alcohols: A Combined Experimental and Computational Mechanistic Investigation

“…By employing allylic alcohols as the electrophiles in the presence of a palladium bis­(phosphine) cocatalyst, regioselective dehydrative N-allylations of various azoles were achieved (Scheme ). − Control experiments showed that the organoboron catalyst has a significant effect on both reaction rate and N-allylation regioselectivity, suggesting that it plays a role both in activating the allylic alcohol electrophile, in cooperation with the Xantphos­(Pd) complex, and the azole nucleophile. , The allylation method has been extended to other NH-pronucleophiles, including pyridones and sulfoximines …”

Stereoselective Synthesis of Tri- and Tetrasubstituted Allylsilanes via Copper-Catalyzed Decarboxylative Silylation of Vinylethylene Carbonates

“…In recent years, a wide array of elegant approaches based on the allylic substitution reactions of vinylethylene carbonates (VECs) have attracted intense attention, due to their ability to afford a variety of allylic compounds via C–X (X = C, N, O, S, B) bond formation. The key progress involves the metal-catalyzed decarboxylative process of VECs to generate the highly reactive zwitterionic intermediate, which can react with nucleophiles to furnish the products.…”