Polymer-supported N-benzyl- and N-benzhydryl-2-nitrobenzenesulfonamides as alternative to aldehyde linkers

Polymer-supported N-benzyl- and N-benzhydryl-2-nitrobenzenesulfonamides 1 were N-alkylated using three different routes: via Fukuyama reaction with alcohols, by N-alkylation with electrophiles, and by Michael addition reaction with α,β-unsaturated carbonyl compounds. The N-alkylated products were obtained in excellent purity and high yield. The 2-nitrobenzenesulfonyl (Nos) group was then cleaved to yield polymer-supported N-alkylated benzylamines and benzhydrylamines. N-alkylation of polymer-supported 2-nitrobenzenesulfonamide linkers 1 described herein represents an alternative route to reductive amination of aldehyde linkers.