Journal
ISRAEL JOURNAL OF CHEMISTRY
Volume 56, Issue 6-7, Pages 399-408Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201500083
Keywords
arenes; C-H insertion; cycloaddition; cyclopropanation; vinylcarbene
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Funding
- National Science Foundation
- National Institutes of Health
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1559715] Funding Source: National Science Foundation
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Select transition metal compounds catalyze metal vinylcarbene formation from cyclopropenes, and their documented reactions include both intermolecular and intramolecular C-H insertion and cyclopropanation, as well as [3+3]-cycloaddition. Although known to undergo carbene-like transformations for decades, the uses of cyclopropenes as reactive alternatives to diazo compounds under mild conditions has been limited. However, recently developed donor-acceptor cyclopropenes that are conveniently accessed from enoldiazoacetates and enoldiazoacetamides are effective metallo-vinylcarbene precursors. They provide entry to highly stereoselective metal carbene transformations under reaction conditions that are milder than those required for dinitrogen extrusion from diazo compounds.
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