4-(Dimethylaminomethyl)phenylacetic acid hydrochloride
CAS Number:
99985-52-1
Molecular Formula:
C11H16ClNO2
C–H insertions in oxidative gold catalysis: synthesis of polycyclic 2H-pyran-3(6H)-ones via a relay strategy
Literature Information
Publication Date
2015-10-14
DOI
10.1039/C5QO00308C
Impact Factor
5.281
Authors
Zhitong Zheng, Liming Zhang
View Original
Abstract
An expedient synthesis of bicyclic/polycyclic 2H-pyran-3(6H)-ones is realized in a cascade cyclization triggered by oxidative gold catalysis and terminated by streamlining C–H insertions. In this reaction, an α-oxo gold carbene intermediate, initially formed upon gold-catalyzed oxidation of alkynes, could be trapped by a tethered C–C triple bond, thereby resulting in the formation of a putative vinyl cation intermediate. This intermediate of high electrophilicity is proposed to be responsible for intramolecular C–H insertions, the mostly concerted nature of which is established by the reactions of chiral substrates. The reaction provides a rapid approach to the construction of functionalized polycyclic systems from easily accessible bispropargyl ethers and with minimal structural prefunctionalization.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
5,5',5''-(((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(oxy))triisophthalic acid
CAS Number:
1159974-70-5
Molecular Formula:
C36H30O15
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