Nickel/Copper Co-catalyzed Enantioselective Reductive Coupling of Oxabenzonorbornadienes with Vinyl Bromides

The enantioselective reductive coupling of oxabenzonorbornadiene with vinyl bromide is developed with earth-abundant nickel catalyst with copper as Lewis acid co-catalyst. The asymmetric reductive coupling is applicable with a wide range of azabenzonorbornadienes and vinyl bromides under nickel/copper co-catalytic system, affording the cis ring-opening vinylation products in good yields with high optical purities. The present study has enabled straightforward stereoselective preparation of chiral 2-vinyl-tetrahydronaphthalens from vinyl halides. image

Automated summary

The enantioselective reductive coupling of oxabenzonorbornadiene with vinyl bromide was developed using earth-abundant nickel catalyst with copper as Lewis acid co-catalyst. The asymmetric reductive coupling is applicable with a wide range of azabenzonorbornadienes and vinyl bromides under nickel/copper co-catalytic system, affording the cis ring-opening vinylation products in good yields with high optical purities. This study enables straightforward stereoselective preparation of chiral 2-vinyl-tetrahydronaphthalens from vinyl halides.