The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Synlett ◽  
2018 ◽  
Vol 30 (07) ◽  
pp. 787-791 ◽  
Author(s):  
David Cain ◽  
Calum McLaughlin ◽  
John Molloy ◽  
Cameron Carpenter-Warren ◽  
Niall Anderson ◽  
...  

Cascade reactions are an important strategy in reaction ­design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki–Miyaura/Diels–Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo­phile for cross-coupling and as a Diels–Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels–Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels–Alder process was also assessed.


2015 ◽  
Vol 35 (3) ◽  
pp. 724
Author(s):  
Yuqin Wu ◽  
Liangyun Yu ◽  
Qi Zhang ◽  
Lidong Li

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