A Flow Microreactor Approach to a Highly Efficient Diels–Alder Reaction with an Electrogenerated o-Quinone

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1194-1198 ◽  
Author(s):  
Kenta Tanaka ◽  
Hirona Yoshizawa ◽  
Mahito Atobe

We have demonstrated a Diels–Alder reaction of an o-quinone generated in an electrochemical flow microreactor. In the flow microreactor system, 4-tert-butyl-o-benzoquinone was easily electrogenerated from 4-tert-butylpyrocatechol in the absence of chemical oxidants and then rapidly used, without decomposing, in a subsequent Diels–Adler reaction with various fulvenes to give the desired products efficiently.

Heterocycles ◽  
2008 ◽  
Vol 76 (1) ◽  
pp. 381 ◽  
Author(s):  
Hiroto Nakano ◽  
Mitsuhiro Takeshita ◽  
Yasuhiro Nishiuchi ◽  
Kouichi Takahashi ◽  
Reiko Fujita ◽  
...  

ChemInform ◽  
2003 ◽  
Vol 34 (16) ◽  
Author(s):  
Haifeng Du ◽  
Jiang Long ◽  
Jieyu Hu ◽  
Xin Li ◽  
Kuiling Ding

2015 ◽  
Vol 51 (55) ◽  
pp. 11130-11133 ◽  
Author(s):  
S. Hörner ◽  
C. Uth ◽  
O. Avrutina ◽  
H. Frauendorf ◽  
M. Wiessler ◽  
...  

A modular bioconjugation strategy based on stepwise oxime ligation and inverse electron-demand Diels–Alder reaction.


2017 ◽  
Vol 53 (10) ◽  
pp. 1657-1659 ◽  
Author(s):  
Jun Li ◽  
Hai-Yan Tao ◽  
Chun-Jiang Wang

A highly efficient enantioselective nitroso Diels–Alder reaction of 6-methyl-2-nitroso pyridine with various 1,3-dienes was successfully developed using a copper(i)/(S)–TF-BiphamPhos complex as the catalyst. For most of the cyclic dienes, the cycloadducts were obtained in high yields with excellent regio-, and stereoselectivities. Acyclic 2-silyloxy-1,3-diene also worked well in the reaction.


Synthesis ◽  
1990 ◽  
Vol 1990 (07) ◽  
pp. 599-603 ◽  
Author(s):  
Georg Kneer ◽  
Jochen Mattay ◽  
Gerhard Raabe ◽  
Carl Krüger ◽  
Jürgen Lauterwein

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