Cycloaddition of Zirconacyclopentadiene with 2-Bromoacrylate, 2-Bromoacrylaldehyde, and 3-Bromofuran-2,5-dione in the Presence of CuCl: A New Pathway for the Formation of Benzene Derivatives and Isobenzofuran-1,3-dione

Abstract

Reaction of zirconacyclopentadienes with 2-bromoalkenes in the presence of CuCl afforded multisubstituted benzene derivatives. The reactions of 2-bromoacrylate and 2-bromo-3-phenylacrylaldehyde afforded penta- and hexasubstituted benzenes in good yields. The reaction of 3-bromofuran-2,5-dione with zirconacyclopentadienes gave isobenzofuran-1,3-diones in good yields.

Keywords:

• 2-Bromoacrylaldehyde
• 2-bromoacrylate
• 3-bromofuran-2,5-dione
• cuprous chloride
• zirconacyclopentadiene

ACKNOWLEDGMENT

We thank the National Natural Science Foundation of China (20172032, 20872076) for supporting this work.

Notes

^a GC yields; isolated yields are given in parentheses.

^a GC yields; isolated yields are given in parentheses.