[Science Journal Cover design] Pd-Catalyzed Stereospecific Cross-Coupling of Chiral α-Borylalkylcopper Species with Aryl Bromides

Science Journal Cover design

A recent study has achieved stereospecific cross-coupling of chiral α-borylalkylcopper species with aryl bromides using a Pd catalyst. The process involves a copper catalyst combined with a chiral NHC ligand to generate enantioenriched secondary α-borylorganocopper species through the addition of Cu–Bpin to alkenyl boramides. The subsequent cross-coupling with aryl bromides, facilitated by a palladium-XPhos catalyst, successfully yields the desired products. Notably, using 1,2-disubstituted borylalkenes with a 1,8-naphthalenediaminatoboryl (Bdan) group results in anti-diborylalkanes as single diastereomers with high enantioselectivity up to 96.5:3.5 er. These compounds can be further oxidized to form anti-1,2-dihydroxyl compounds. -Journal cover design by scapiens

https://pubs.acs.org/doi/10.1021/acscatal.9b05213

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