Selective carbon-carbon bond formation via transition-metal catalysis. 33. Palladium-catalyzed cross-coupling reaction of .alpha.-heterosubstituted alkenylmetals. A stereoselective route to heterosubstituted dienes suitable for the Diels-Alder reaction

1983 ◽  
Vol 48 (9) ◽  
pp. 1560-1562 ◽  
Author(s):  
Eiichi Negishi ◽  
Fentair Luo
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Diels Alder Reaction ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1947-1958
Author(s):  
Tsutomu Konno ◽  
Gen Egashira ◽  
Chihiro Kajimoto ◽  
Takuto Kataoka ◽  
Shigeyuki Yamada
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Benzene Derivatives ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Oxidative Aromatization ◽  
High Yields ◽  
Acetylene Derivatives

On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd(PPh3)4 to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoro­ethylene group.

Transition metal catalysis of the diels-alder reaction

1991 ◽  
Vol 32 (39) ◽  
pp. 5299-5302 ◽  
Author(s):  
Alan S. Olson ◽  
William J. Seitz ◽  
M. Mahmun Hossain
Keyword(s):  
Transition Metal ◽  
Alder Reaction ◽  
Diels Alder ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Diels Alder Reaction
Sign in / Sign up

Export Citation Format

Share Document