Mechanistic Studies of the Palladium-Catalyzed Ring Opening of Oxabicyclic Alkenes with Dialkylzinc

2001 ◽  
Vol 123 (28) ◽  
pp. 6834-6839 ◽  
Author(s):  
Mark Lautens ◽  
Sheldon Hiebert ◽  
Jean-Luc Renaud
Keyword(s):  
Ring Opening ◽  
Mechanistic Studies ◽  
Palladium Catalyzed ◽  
Oxabicyclic Alkenes

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

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

2004 ◽  
Vol 6 (16) ◽  
pp. 2833-2835 ◽  
Author(s):  
Ming Li ◽  
Xiao-Xia Yan ◽  
Wei Hong ◽  
Xia-Zhen Zhu ◽  
Bo-Xun Cao ◽  
...  
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Oxabicyclic Alkenes

Palladium-Catalyzed syn-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides

2019 ◽  
Vol 84 (19) ◽  
pp. 12481-12489 ◽  
Author(s):  
Donghan Chen ◽  
Yongqi Yao ◽  
Wen Yang ◽  
Qifu Lin ◽  
Huanyong Li ◽  
...  
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Oxabicyclic Alkenes
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