Silver-Catalyzed Allylation of Ketones and Intramolecular Cyclization through Carbene Intermediates from Cyclopropenes Under Ambient Conditions

• Published in: Chemistry, an Asian journal Vol. 11; no. 5; pp. 713 - 721
• Main Authors: Nakano, Takeo, Endo, Kohei, Ukaji, Yutaka
• Format: Journal Article
• Language: English
• Published: Germany Blackwell Publishing Ltd 04.03.2016; Wiley Subscription Services, Inc
• Subjects: allylation; carbenoids; Chemistry; silver; zinc; carbenoids; silver; allylation; zinc
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201501196

Tandem C−C bond formation was achieved through silver‐catalyzed ring‐opening of cyclopropenes via carbene intermediates. The reaction of cyclopropenes in the presence of a silver catalyst gave indene derivatives under ambient conditions. In contrast, the insertion of organozinc reagents to silver carbene or allylic cation intermediates afforded allylmetal intermediates for the tandem allylation of carbonyl compounds. Two for the price of 1: Tandem C−C bond formation was achieved through silver‐catalyzed ring‐opening of cyclopropenes via carbene intermediates. The reaction of cyclopropenes in the presence of a silver catalyst gave indene derivatives under ambient conditions. In contrast, the insertion of organozinc reagents to silver carbene or allylic cation intermediates afforded allylmetal intermediates for the tandem allylation of carbonyl compounds.