Inverse-electron-demand Diels-Alder reactions of Fischer carbene complexes: a new and efficient dihydrobenzene synthesis via a retrocycloaddition of chromium hexacarbonyl

1990 ◽  
Vol 112 (11) ◽  
pp. 4550-4552 ◽  
Author(s):  
Siu Ling B. Wang ◽  
William D. Wulff
Keyword(s):  
Diels Alder ◽  
Fischer Carbene Complexes ◽  
Carbene Complexes ◽  
Fischer Carbene ◽  
Inverse Electron Demand ◽  
Chromium Hexacarbonyl ◽  
Electron Demand

scholarly journals One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

2010 ◽  
Vol 6 ◽  
Author(s):  
Priyabrata Roy ◽  
Binay Krishna Ghorai
Keyword(s):  
Diels Alder ◽  
Fischer Carbene Complexes ◽  
One Pot ◽  
Carbene Complexes ◽  
Ring Systems ◽  
First Report ◽  
Fischer Carbene ◽  
Carbonyl Derivatives ◽  
Transient Intermediates ◽  
Three Component Coupling

One-pot three-component coupling ofo-alkynylheteroaryl carbonyl derivatives with Fischer carbene complexes and dienophiles leading to the synthesis of quinoxaline and phenazine ring systems has been investigated. This involves the generation of furo[3,4-b]pyrazine and furo[3,4-b]quinoxaline as transient intermediates, which were trapped with Diels–Alder dienophiles. This is the first report on furo[3,4-b]pyrazine intermediates.

Diels-Alder reactions of Fischer carbene complexes

1983 ◽  
Vol 105 (22) ◽  
pp. 6726-6727 ◽  
Author(s):  
William D. Wulff ◽  
Dominic C. Yang
Keyword(s):  
Diels Alder ◽  
Fischer Carbene Complexes ◽  
Carbene Complexes ◽  
Fischer Carbene

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

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