Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 4, Pages 1449-1453Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404990
Keywords
carbenes; C-H insertion; iodonium ylides; lactams; reaction mechanism
Categories
Funding
- Fundacao para a Ciencia e Tecnologia [SFRH/DB/61220/2009, PTDC/QUI-QUI/119823/2010, PEst-OE/QUI/UI0100/2013, PEst-OE/SAU/UI4013/2011, REDE/1518/REM/2005]
- Accoes Integradas Luso-Alemas [A-14/11]
- Max-Plank Institut fur Kohlenforschung
- Fundação para a Ciência e a Tecnologia [PTDC/QUI-QUI/119823/2010] Funding Source: FCT
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Carbene intermediates are very useful species for a range of reactions including C-H insertions and cycloadditions. They are most commonly generated by metal-catalyzed release of nitrogen gas from diazo precursors. Herein, we present a novel C-H insertion of simple b-ketoamide substrates, through reaction with (diacetoxyiodo) benzene (DIB) in the presence of a base. This unprecedented transformation bypasses the use of either diazo precursors or metal catalysts and directly delivers beta-lactam products by an iodonium ylide, in a single step under mild conditions. Mechanistic studies support the intermediacy of a free singlet carbene of unique reactivity and selectivity.
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