Palladium-catalyzed carbonylation of aryl tosylates and mesylates.
A general protocol for the palladium-catalyzed carbonylation of aryl tosylates and mesylates to form esters has been developed using a catalyst system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand. The system operates under mild conditions: atmospheric CO pressure and temperatures of 80-110 degrees C. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance.
Munday
Rachel H
RH
Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Martinelli
Joseph R
JR
Buchwald
Stephen L
SL
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D000438:Alcohols; D004952:Esters; D008024:Ligands; D008698:Mesylates; D009942:Organometallic Compounds; D014105:Tosyl Compounds; D010165:Palladium