Asymmetric Alkene Boration and Z -Retentive Allylic Substitution Reactions under Cu/Pd Relay Catalysis
Abstract
Cu/Pd-cocatalyzed cascade asymmetric alkene boration and Z -retentive allylic substitution reactions are described. Taking advantage of palladium catalysts that well tune the rates of both the π–σ–π isomerization process of the π-allyl-palladium species and nucleophilic substitution, either Z -retentive or Z -to- E allylic substitution reactions can be achieved, with alkyl copper nucleophiles generated in situ via Cu-catalyzed alkene boration. Chiral Z - and E -olefins containing an organoboronate functional group are afforded under Cu/Pd relay catalysis from the same starting materials. Both reactions proceed with high yields (up to 95%), excellent Z / E ratios (up to >19:1), and good enantioselectivity (up to 94% ee).
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Organoboron and organosilicon chemistry
Boron Compounds in Chemistry
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 14
- Pages
- 14846–14854
- Publication date
- 3 April 2026
- Language
- EN