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Gold‐Catalyzed Formal C−C Bond Insertion Reaction of 2‐Aryl‐2‐diazoesters with 1,3‐Diketones.
- Source :
- Chemistry - An Asian Journal; Sep2018, Vol. 13 Issue 18, p2606-2610, 5p
- Publication Year :
- 2018
-
Abstract
- Abstract: The transition‐metal‐catalyzed formal C−C bond insertion reaction of diazo compounds with monocarbonyl compounds is well established, but the related reaction of 1,3‐diketones instead gives C−H bond insertion products. Herein, we report a protocol for a gold‐catalyzed formal C−C bond insertion reaction of 2‐aryl‐2‐diazoesters with 1,3‐diketones, which provides efficient access to polycarbonyl compounds with an all‐carbon quaternary center. The aryl ester moiety plays a crucial role in the unusual chemoselectivity, and the addition of a Brønsted acid to the reaction mixture improves the yield of the C−C bond insertion product. A reaction mechanism involving cyclopropanation of a gold carbenoid with an enolate and ring‐opening of the resulting donor–acceptor‐type cyclopropane intermediate is proposed. This mechanism differs from that of the traditional Lewis‐acid‐catalyzed C−C bond insertion reaction of diazo compounds with monocarbonyl compounds, which involves a rearrangement of a zwitterion intermediate as a key step. [ABSTRACT FROM AUTHOR]
- Subjects :
- GOLD
CATALYSIS
KETONES
CHEMICAL reactions
DRYING agents
Subjects
Details
- Language :
- English
- ISSN :
- 18614728
- Volume :
- 13
- Issue :
- 18
- Database :
- Complementary Index
- Journal :
- Chemistry - An Asian Journal
- Publication Type :
- Academic Journal
- Accession number :
- 131839038
- Full Text :
- https://doi.org/10.1002/asia.201800934