Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates

2019 ◽  
Vol 84 (13) ◽  
pp. 8724-8730 ◽  
Author(s):  
Giri Raj Gnawali ◽  
Nigam P. Rath ◽  
Christopher D. Spilling
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Vinyl Phosphonates

α,β-Diaryl unsaturated ketones via palladium-catalyzed ring-opening of cyclopropenones with organoboronic acids

2018 ◽  
Vol 5 (10) ◽  
pp. 1651-1654 ◽  
Author(s):  
Lidong Shan ◽  
Ge Wu ◽  
Miaochang Liu ◽  
Wenxia Gao ◽  
Jinchang Ding ◽  
...  
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Unsaturated Ketones ◽  
Organoboronic Acids ◽  
Palladium Catalyzed

Palladium-catalyzed ring-opening acylation of cyclopropenones with organoboronic acids (aryl and vinylboronic acids) at room temperature has been developed to synthesise α,β-diaryl unsaturated ketones with good yields and excellent stereospecificity.

scholarly journals Palladium-catalyzed α-arylation for the addition of small rings to aromatic compounds

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Zhi-Tao He ◽  
John F. Hartwig
Keyword(s):  
Electronic Properties ◽  
Aromatic Compounds ◽  
Ring Opening ◽  
Biologically Active ◽  
High Yield ◽  
Protecting Group ◽  
Mechanistic Studies ◽  
Claisen Condensation ◽  
Wide Range ◽  
Palladium Catalyzed

Abstract Small, strained rings have rigid, defined conformations and unique electronic properties. For these reasons, many groups seek to use these subunits to form biologically active molecules. We report a generally applicable approach to attach small rings to a wide range of aromatic compounds by palladium-catalyzed α-arylation of cyclopropyl, cyclobutyl and azetidinyl esters. The direct α-arylation of cyclopropyl esters and cyclobutyl esters is achieved in high yield by ensuring that the rate of coupling exceeds the rate of Claisen condensation. The α-arylation of azetidines is achieved without ring opening of the strained saturated heterocycle by conducting the reactions with an azetidine derivative bearing a benzyl protecting group on nitrogen. Mechanistic studies show that the α-arylation of small rings is challenging because of the weak acidity of α C-H bond (cyclopropanes), strong sensitivity of the strained esters to Claisen condensation (cyclobutatanes), or facile decomposition of the enolates (azetidinyl esters).

scholarly journals Palladium-Catalyzed Enantioselective Ring Opening of Oxabicyclic Alkenes with Organozinc Halides.

ChemInform ◽  
2004 ◽  
Vol 35 (46) ◽  
Author(s):  
Ming Li ◽  
Xiao-Xia Yan ◽  
Wei Hong ◽  
Xia-Zhen Zhu ◽  
Bo-Xun Cao ◽  
...  
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Oxabicyclic Alkenes
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