Catalytic alkylation reactions of weakly acidic carbonyl and related compounds using alkenes as electrophiles

2018 ◽  
Vol 16 (33) ◽  
pp. 5969-5972 ◽  
Author(s):  
Yasuhiro Yamashita ◽  
Ryo Igarashi ◽  
Hirotsugu Suzuki ◽  
Shū Kobayashi

Catalytic alkylation reactions of weakly acidic carbonyl and related pronucleophiles such as amides, esters, and sulfonamides with substituted alkenes have been reported.

2008 ◽  
Vol 130 (31) ◽  
pp. 10076-10077 ◽  
Author(s):  
Thomas A. Moss ◽  
David R. Fenwick ◽  
Darren J. Dixon

ChemInform ◽  
2013 ◽  
Vol 44 (42) ◽  
pp. no-no
Author(s):  
Magnus Rueping ◽  
Boris J. Nachtsheim

ChemInform ◽  
2008 ◽  
Vol 39 (50) ◽  
Author(s):  
Thomas A. Moss ◽  
David R. Fenwick ◽  
Darren J. Dixon

Synlett ◽  
2018 ◽  
Vol 29 (14) ◽  
pp. 1807-1813 ◽  
Author(s):  
Zhi Li ◽  
Xiao-Long Xu

Alkylation of p-quinones with allylic and benzylic esters is achieved by using a strong Lewis acid as the catalyst. This transformation likely follows an unusual redox chain mechanism. In this mechanism, quinone undergoes a sequence of reactions: it is reduced to ­hydroquinone (HQ), functionalized in a Lewis acid-catalyzed Friedel–Crafts alkylation, and then oxidized back to quinone. The last step is concurrent with the first step of a second quinone molecule, which is reduced to new HQ and functionalized, and thus propagates the redox chain reaction. The autoinitiation mechanism of the redox chain is not well understood, but additive HQ or Hantzsch ester can serve as effective initiators. The likelihood of this mechanism was elaborated by ­kinetic studies and various control experiments.1 Introduction2 Discovery of Catalytic Alkylation Reactions of Quinones3 Proposed Redox Chain Reaction Mechanism and Experimental Evidence4 Substrate Scope5 Conclusion


2013 ◽  
Author(s):  
A. V. Kalueff ◽  
A. M. Stewart ◽  
V. Gjeloshi ◽  
D. Kondaveeti ◽  
N. Neelkantan ◽  
...  
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