An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.
The use of 3,4,7,8-tetramethyl-1,10-phenanthroline (Me(4)Phen) as a ligand improves the Cu-catalyzed cross-coupling reactions of aryl iodides and bromides with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols. Most importantly, by employing this catalyst system, the need to use an excessive quantity of the alcohol coupling partner is alleviated. The relatively mild conditions, short reaction times, and moderately low catalyst loading allow for a wide array of functional groups to be tolerated on both the electrophilic and nucleophilic coupling partners.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Ryan A
RA
Altman
Alexandr
A
Shafir
Alice
A
Choi
Phillip A
PA
Lichtor
Stephen L
SL
Buchwald
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D004987:Ethers; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D003300:Copper