Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 51, Pages 20325-20334Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b10689
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Funding
- EPSRC [EP/S017801/1]
- EU [792439]
- Engineering and Physical Sciences Research Council [EP/L011999/1] Funding Source: researchfish
- EPSRC [EP/L011999/1, EP/S017801/1] Funding Source: UKRI
- Marie Curie Actions (MSCA) [792439] Funding Source: Marie Curie Actions (MSCA)
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[1.1.1]Propellane is a highly strained tricyclic hydrocarbon whose reactivity is dominated by addition reactions across the central inverted bond to provide bicyclo[1.1.1]pentane derivatives. These reactions proceed under both radical and two-electron pathways, hence, providing access to a diverse array of products. Conversely, transition metal-catalyzed reactions of [1.1.1]propellane are underdeveloped and lack synthetic utility, with reported examples generally yielding mixtures of ring-opened structural isomers, dimers, and trimers, often with poor selectivity. Herein, we report that nickel(0) catalysis enables the use of [1.1.1]propellane as a carbene precursor in cyclopropanations of a range of functionalized alkenes to give methylenespiro[2.3]hexane products. Computational studies provide support for initial formation of a Ni(0)-[1.1.1]propellane complex followed by concerted double C-C bond activation to give the key 3-methylenecyclobutylidene-nickel intermediate.
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