p-Methoxybenzyl ether cleavage by polymer-supported sulfonamides.
[reaction: see text] p-Methoxybenzyl ethers have been found to transfer from alcohols to sulfonamides in the presence of catalytic trifluoromethanesulfonic acid. This process for protecting group removal can be performed in solution with yields >94%. Through the use of sulfonamide-functionalized ("safety-catch") resins, p-methoxybenzyl ethers can be cleaved in excellent yields with minimal purification.
Hinklin
Ronald J
RJ
Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Kiessling
Laura L
LL
D000438:Alcohols / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D008698:Mesylates; D011108:Polymers; D013449:Sulfonamides / Q000737:chemistry*
D000438:Alcohols; D001593:Benzyl Compounds; D007202:Indicators and Reagents; D008698:Mesylates; D011108:Polymers; D013449:Sulfonamides; C012077:trifluoromethanesulfonic acid