Journal
ORGANIC LETTERS
Volume 19, Issue 24, Pages 6646-6649Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03374
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Funding
- NNSFC [21522202, 21502017]
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An efficient silver-catalyzed [2 + 1] cyclopropanation of sterically hindered internal alkenes with diazo compounds in which room temperature-decomposable N-nosylhydrazones are used as diazo surrogates is reported. The unexpected unique catalytic activity of silver was ascribed to its dual role as a Lewis acid activating alkene substrates and as a transition metal forming silver carbenoids. A wide range of internal alkenes, including challenging diarylethenes, were suitable for this protocol, thereby affording a variety of cyclopropanes with high efficiency in a stereoselective manner under mild conditions.
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