Reactivity of Stabilized Vinyl Diazo Derivatives toward Unsaturated Hydrocarbons: Regioselective Gold-Catalyzed Carbon-Carbon Bond Formation

They struck gold! New reaction modes were observed in the gold‐catalyzed reaction of alkenyldiazo compounds and unsaturated substrates. The process represents a new CC bond‐formation reaction in which alkenes, alkynes, and arenes are active reagents for the Cγ‐allylation, ‐allenylation, and ‐arylat...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-01, Vol.19 (5), p.1573-1576
Main Authors: Barluenga, José, Lonzi, Giacomo, Tomás, Miguel, López, Luis A.
Format: Article
Language:English
Subjects:
Alkenes
Alkynes
arenes
Aromatic compounds
Bonding
Carbon-carbon composites
Chemistry
Derivatives
diazo compounds
gold
Hydrocarbons
Unsaturated
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Summary:They struck gold! New reaction modes were observed in the gold‐catalyzed reaction of alkenyldiazo compounds and unsaturated substrates. The process represents a new CC bond‐formation reaction in which alkenes, alkynes, and arenes are active reagents for the Cγ‐allylation, ‐allenylation, and ‐arylation, respectively, of alkenyldiazo substrates (see scheme). The reactivity pattern is likely to rely on the formation of a highly electrophilic alkenylgold carbenoid, which may be involved in a carbocation‐type mechanism.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201203217