Vinyl cation intermediates in solvolytic and electrophilic reactions. 2. Bromination of arylacetylenes

1980 ◽  
Vol 45 (19) ◽  
pp. 3902-3906 ◽  
Author(s):  
Keith Yates ◽  
George Mandrapilias
Keyword(s):  
Electrophilic Reactions ◽  
Vinyl Cation

Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Biologically Active ◽  
Dft Studies ◽  
Thermodynamic Control ◽  
Important Goal ◽  
Peptide Bonds ◽  
Metal Free ◽  
Vinyl Cation ◽  
E And Z Isomers ◽  
Vinyl Fluorides

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>

Carbenoids with neighboring heteroatoms. III. Electrophilic reactions of two .alpha.-halocyclopropyllithium compounds

1972 ◽  
Vol 37 (15) ◽  
pp. 2436-2443 ◽  
Author(s):  
K. Grant. Taylor ◽  
W. Edward. Hobbs ◽  
Melvin S. Clark ◽  
James. Chaney
Keyword(s):  
Electrophilic Reactions
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