Direct conversion of alcohols to acetals and H(2) catalyzed by an acridine-based ruthenium pincer complex.
The crystallographically characterized ruthenium complex RuHCl(A-(i)Pr-PNP)(CO) (1) [A-(i)Pr-PNP = 4,5-bis-(diisopropylphosphinomethyl)acridine], which bears a nonplanar acridine moiety, catalyzes in a neutral medium the transformation of primary alcohols to the corresponding acetals with the liberation of H(2). In the presence of base, complex 1 catalyzes the dehydrogenative coupling of alcohols to form esters. Acetal formation may involve hemiacetal dehydration to form an enol ether followed by alcohol addition to the double bond.
Gunanathan
Chidambaram
C
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel.
Shimon
Linda J W
LJ
Milstein
David
D
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000166:Acridines / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D000080:Acetals; D000166:Acridines; D000438:Alcohols; D009942:Organometallic Compounds; D012428:Ruthenium; D006859:Hydrogen