N to C aryl migration in lithiated carbamates: α-arylation of benzylic alcohols

Jonathan Clayden*, William Farnaby, Damian M. Grainger, Ulrich Hennecke, Michele Mancinelli, Daniel J. Tetlow, Ian H. Hillier, Mark A. Vincent

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

42 Citations (Scopus)

Abstract

We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to @,@-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.

Original languageEnglish
Pages (from-to)3410-3411
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number10
Early online date18 Feb 2009
DOIs
Publication statusPublished - 18 Mar 2009

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