Rapid Bis‐Coupling Reactivity with Triarylbismuth Reagents: Synthesis of Structurally Diverse Scaffolds and Step‐economic Convergent Synthesis of Quebecol

• Published in: European journal of organic chemistry Vol. 2020; no. 11; pp. 1629 - 1636
• Main Authors: Rao, Maddali L. N., Murty, Venneti N., Nand, Sachchida
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 22-03-2020
• Subjects: Acrylates; Alkynes; Aromatic compounds; Convergence; Cross coupling; Esters; Natural products; Palladium; Palladium catalysis; Quebecol synthesis; Reagents; Scaffolds; Synthesis; Triarylbismuth reagents; Trisubstituted acrylates
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901830

The cross‐coupling study of gem‐dibromoesters with triarylbismuths as threefold arylating reagents was investigated under palladium‐catalyzed conditions. This study using triarylbismuth reagents explored the cross‐coupling reactivity with various functionalized gem‐dibromoesters. It furnished a variety of multi‐functional trisubstituted acrylates embedded with aryl, alkene and alkyne scaffolds in high yields. The present study in turn, provided easy access to various triarylated acrylates and functionalized 1,3‐dienyl and 1,3‐enyne esters. Further, the established method applied in the step‐economic and convergent synthesis of quebecol natural product in good yield.
The cross‐coupling study of gem‐dibromoesters with triarylbismuths furnished a variety of multi‐functional trisubstituted acrylates embedded with aryl, alkene and alkyne scaffolds in high yields under palladium catalysis. Further, the established method was applied in the step‐economic and convergent synthesis of quebecol natural product in good yield.