Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids.
A mild, functional group tolerant method of the preparation of phenyl esters from aryl chlorides via palladium-catalyzed carbonylation is described using atmospheric pressure of carbon monoxide. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions. Direct preparation of alkyl esters and carboxylic acids is also demonstrated, providing the first method for the preparation of methyl and ethyl esters from aryl chlorides without pressured reactors.
Watson
Donald A
DA
Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fan
Xuexiang
X
Buchwald
Stephen L
SL
D001274:Atmospheric Pressure; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D001565:Benzoates; D004952:Esters; D006843:Hydrocarbons, Chlorinated; D010165:Palladium; D002248:Carbon Monoxide; D010100:Oxygen