Conjugate Addition vs Heck Reaction: A Theoretical Study on Competitive Coupling Catalyzed by Isoelectronic Metal (Pd(II) and Rh(I))

2012 ◽  
Vol 77 (17) ◽  
pp. 7487-7496 ◽  
Author(s):  
Qian Peng ◽  
Hong Yan ◽  
Xinhao Zhang ◽  
Yun-Dong Wu
2008 ◽  
Vol 26 (2) ◽  
pp. 358-362 ◽  
Author(s):  
Chen WANG ◽  
Yao FU ◽  
Zhe LI ◽  
Qing-Xiang GUO

2005 ◽  
Vol 7 (25) ◽  
pp. 5629-5632 ◽  
Author(s):  
Gabriela de la Herrán ◽  
Carmen Murcia ◽  
Aurelio G. Csákÿ

2011 ◽  
Vol 17 (11) ◽  
pp. 3091-3095 ◽  
Author(s):  
Aditya L. Gottumukkala ◽  
Johannes G. de Vries ◽  
Adriaan J. Minnaard

2014 ◽  
Vol 33 (19) ◽  
pp. 5111-5119 ◽  
Author(s):  
Esra Boz ◽  
Z. Pınar Haşlak ◽  
Nurcan Ş. Tüzün ◽  
F. Aylin Sungur Konuklar

2015 ◽  
Vol 16 (0) ◽  
pp. 30-38
Author(s):  
Shohei Sanada ◽  
Takaaki Kuroda ◽  
Michinori Sumimoto ◽  
Kenji Hori

2000 ◽  
Vol 65 (5) ◽  
pp. 797-804 ◽  
Author(s):  
Martina Havelková ◽  
Martin Studenovský ◽  
Dalimil Dvořák

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alkylhypoxanthine derivatives. Formation of these unexpected products can be rationalised as a Tl+- or Ag+-assisted substitution of halogen with acetate anion. The 6-acetoxypurine derivative thus formed then eliminates ketene and gives 7-benzyl- or 9-benzylhypoxanthine. Conjugate addition of these compounds onto Michael acceptors furnishes the N1-substituted hypoxanthine derivatives.


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