Hiyama coupling

<p>The Hiyama coupling is a <a href="/facts/Palladium/AXMwDFxs">palladium</a>-catalyzed <a href="/facts/Cross_coupling_reaction/cF8RBvCx">cross-coupling reaction</a> of <a href="/facts/Organosilicon/JvUwzDQ4">organosilanes</a> with <a href="/facts/Halocarbon/FTmWVdPT">organic halides</a> used in <a href="/facts/Organic_chemistry/djxhxaNg">organic chemistry</a> to form <a href="/facts/Carbon%E2%80%93carbon_bond/nLE4z5BK">carbon–carbon bonds</a> (C-C bonds). This reaction was discovered in 1988 by <a href="/facts/Tamejiro_Hiyama/zoeAmv4D">Tamejiro Hiyama</a> and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with <a href="/facts/Chemoselectivity/hy4R50B3">chemo</a>- and <a href="/facts/Regioselectivity/m3Bs2Xzl">regioselectivity</a>. The Hiyama coupling has been applied to the synthesis of various <a href="/facts/Natural_product/J4RsVhmP">natural products</a>. 
</p>

R
                    
                      −
                    
                    
                      SiR
                      
                        3
                      
                      
                        ″
                        
                          
                        
                      
                    
                  
                  +
                  
                    R
                    ′
                  
                  
                    −
                  
                  X
                  
                    
                      →
                      
                        
                          Pd cat.
                        
                      
                      
                        
                          
                            F
                            
                              −
                            
                          
                        
                      
                    
                  
                  R
                  
                    −
                  
                  
                    R
                    ′
                  
                
              
            
          
        
      
    
    {\displaystyle {\begin{matrix}{}\\{\ce {{R-SiR''_{3}}+R'-X->[\mathrm {F^{-}} ][{\text{Pd cat.}}]R-R'}}\end{matrix}}}

<ul><li>
  
    
      
        
          R
        
      
    
    {\displaystyle {\ce {R}}}
  
: aryl, alkenyl or alkynyl</li>
<li>
  
    
      
        
          
            R
            ′
          
        
      
    
    {\displaystyle {\ce {R'}}}
  
: aryl, alkenyl, alkynyl or alkyl</li>
<li>
  
    
      
        
          
            R
            ″
          
        
      
    
    {\displaystyle {\ce {R''}}}
  
: Cl, F or alkyl</li>
<li>
  
    
      
        
          X
        
      
    
    {\displaystyle {\ce {X}}}
  
: Cl, Br, I or OTf</li></ul>

Hiyama coupling open-in-new

Hiyama coupling