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Ligand Controlled Highly Selective Copper‐Catalyzed Borylcuprations of Allenes with Bis(pinacolato)diboron
Author(s) -
Yuan Weiming,
Ma Shengming
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100929
Subject(s) - chemistry , regioselectivity , ligand (biochemistry) , phosphine , denticity , medicinal chemistry , catalysis , copper , aryl , tris , stereochemistry , combinatorial chemistry , organic chemistry , crystal structure , receptor , biochemistry , alkyl
Copper‐catalyzed highly selective borylcuprations of allenes with bis(pinacolato)diboron produce two different types of alkenylboranes by applying a ligand effect. In the presence of tris( para ‐methoxyphenyl)phosphine [P(C 6 H 4 OMe‐ p ) 3 ], the reaction of aryl‐1,2‐dienes affords 2‐alken‐2‐yl boronates as the only product with exclusive Z ‐geometry; the regioselectivity is switched to afford the 1‐alken‐2‐yl boronates as the major products when the bidentate phosphine 2,2′‐bis(diphenylphosphino)biphenyl is used as the ligand.