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Journal Article
Research Support, Non-U.S. Gov't
Ring-selective functionalization of N,N'-diarylureas by regioselective N-alkylation and directed ortho metalation.
Organic Letters 2005 July 22
[reaction: see text]. Unsymmetrical N,N'-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.
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