Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration.
We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.
Imao
Daisuke
D
Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 3N6.
Glasspoole
Ben W
BW
Laberge
Véronique S
VS
Crudden
Cathleen M
CM
D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry; D013237:Stereoisomerism
D001896:Boron Compounds; D004952:Esters; D009943:Organophosphorus Compounds; D010087:Oxides; D018030:Silver Compounds; C061896:triphenylphosphine; D010165:Palladium; C040225:disilver oxide