Castro-Stephens coupling | Wikipedia audio article
Channel: wikipedia tts
Date: 2019-02-20

This is an audio version of the Wikipedia Article:
https://en.wikipedia.org/wiki/Castro%E2%80%93Stephens_coupling





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SUMMARY
=======
The Castro–Stephens coupling is a cross coupling reaction between a copper(I) acetylide and an aryl halide in pyridine, forming a disubstituted alkyne and a copper(I) halide.
[{\ce {pyridine}}]CuX}}+{\color {Red}{\ce {R}}{-}}{\ce {C{\equiv }C-R'}}\\{\color {Red}{\ce {X}}}&={\color {Red}{\ce {I,Br,Cl}}}\\{\color {Red}{\ce {R}}}&={\color {Red}{\ce {Ar}}}\end{aligned}}}"
  
    
      
        
          
            
              
                

                
              
            
            
              
                
                  Cu
                  
                    −
                  
                  C
                  
                    ≡
                  
                  C
                  
                    −
                  
                  
                    R
                    ′
                  
                
                +
                
                  
                    
                      R
                      
                        −
                      
                      X
                    
                  
                
                 
              
              
                
                
                  
                    
                      →
                      
                        
                          pyridine
                        
                      
                    
                  
                  CuX
                
                +
                
                  
                    
                      R
                    
                    
                      −
                    
                  
                
                
                  C
                  
                    ≡
                  
                  C
                  
                    −
                  
                  
                    R
                    ′
                  
                
              
            
            
              
                
                  
                    
                      X
                    
                  
                
              
              
                
                =
                
                  
                    
                      I
                      ,
                      Br
                      ,
                      Cl
                    
                  
                
              
            
            
              
                
                  
                    
                      R
                    
                  
                
              
              
                
                =
                
                  
                    
                      Ar
                    
                  
                
              
            
          
        
      
    
    {\displaystyle {\begin{aligned}{}\\{\ce {Cu-C{\equiv }C-R'}}+{\color {Red}{\ce {R-X}}}\ &{\ce {-[{\ce {pyridine}}]CuX}}+{\color {Red}{\ce {R}}{-}}{\ce {C{\equiv }C-R'}}\\{\color {Red}{\ce {X}}}&={\color {Red}{\ce {I,Br,Cl}}}\\{\color {Red}{\ce {R}}}&={\color {Red}{\ce {Ar}}}\end{aligned}}}
  The reaction was discovered in 1963 by University of California, Riverside chemists Castro and Stephens and is used as a tool in the organic synthesis of organic compounds. The reaction has similarities with the much older Rosenmund–von Braun synthesis (1914) between aryl halides and copper(I) cyanide and was itself modified in 1975 with as the Sonogashira coupling by adding a palladium catalyst and preparing the organocopper compound in situ, allowing copp ...