Stille reaction

The Stille reaction is a <a href="/facts/Chemical_reaction/GpqWlKrz">chemical reaction</a> widely used in <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a>. The reaction involves the coupling of two organic groups, one of which is carried as an <a href="/facts/Organotin_chemistry/B4aDa9Lq">organotin compound</a> (also known as organostannanes). A variety of organic electrophiles provide the other <a href="/facts/Coupling_partner/1PpYXgkI">coupling partner</a>. The Stille reaction is one of many <a href="/facts/Cross-coupling_reaction/cF8RBvCx">palladium-catalyzed coupling reactions</a>.

R
                
                  1
                
              
              
                −
              
              Sn
              
                
                  (
                  Alkyl
                  )
                
                
                  3
                
                
                  
                
              
            
          
        
        +
        
          
            
              
                R
                
                  2
                
              
              
                −
              
              X
            
          
        
         
        
          
            
              →
              
                
                  ligand set
                
              
              
                
                  
                    
                      
                        Pd
                        
                          0
                        
                      
                    
                  
                
                
                   (catalytic)
                
              
            
          
        
         
        
          
            
              
                
                  
                    
                      
                        R
                        
                          1
                        
                      
                    
                  
                
                
                −
                
                
                  
                    
                      
                        R
                        
                          2
                        
                      
                    
                  
                
              
              ⏞
            
          
          
            c
            o
            u
            p
            l
            e
            d
             
            p
            r
            o
            d
            u
            c
            t
          
        
        +
        
          
            
              X
            
          
        
        
        −
        
        
          
            
              Sn
              
                
                  (
                  Alkyl
                  )
                
                
                  3
                
                
                  
                
              
            
          
        
      
    
    {\displaystyle {\color {Blue}{\ce {R^{1}-Sn(Alkyl)3}}}+{\color {Red}{\ce {R^{2}-X}}}\ {\ce {->[{\color {Green}{\ce {Pd^{0}}}}{\text{ (catalytic)}}][{\text{ligand set}}]}}\ \overbrace {{\color {Blue}{\ce {R^{1}}}}\!-\!{\color {Red}{\ce {R^{2}}}}} ^{coupled\ product}+{\color {Red}{\ce {X}}}\!-\!{\color {Blue}{\ce {Sn(Alkyl)3}}}}

<ul><li>
 
 
 
 
 
 
 
 R
 
 1
 
 
 
 
 
 
 ,
  
 
 
 
 
 R
 
 2
 
 
 
 
 
 
 
 {\displaystyle {\color {Blue}{\ce {R^1}}}\!,\ {\color {Red}{\ce {R^2}}}}
 
: Allyl, alkenyl, aryl, benzyl, acyl</li>
<li>
 
 
 
 
 
 
 X
 
 
 
 
 
 {\displaystyle {\color {Red}{\ce {X}}}}
 
: halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc</li></ul>
The R1 group attached to the trialkyltin is normally sp2-hybridized, including <a href="/facts/Vinyl_group/SyXSgVnw">vinyl</a>, and <a href="/facts/Aryl/M3z7QRXd">aryl</a> groups.
These organostannanes are also stable to both air and moisture, and many of these reagents either are commercially available or can be synthesized from literature precedent. However, these tin reagents tend to be highly toxic. X is typically a <a href="/facts/Halide/ujYu8kGD">halide</a>, such as <a href="/facts/Chlorine/y27UwYBM">Cl</a>, <a href="/facts/Bromine/oLfj3C7D">Br</a>, or <a href="/facts/Iodine/JlfMecMf">I</a>, yet pseudohalides such as <a href="/facts/Triflate/6sbvDSyt">triflates</a> and <a href="/facts/Sulfonate/ApbgQMXB">sulfonates</a> and <a href="/facts/Phosphate/FDGVCxUG">phosphates</a> can also be used. Several reviews have been published.[excessive citations]

Stille reaction open-in-new

Stille reaction