scholarly journals An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

2018 ◽  
Vol 14 ◽  
pp. 618-625 ◽  
Author(s):  
Longcheng Hong ◽  
Sebastian Ahles ◽  
Andreas H Heindl ◽  
Gastelle Tiétcha ◽  
Andrey Petrov ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Acid Catalyst ◽  
Diels Alder ◽  
Organic Transformations ◽  
Nmr Studies ◽  
One Pot ◽  
Efficient Catalyst ◽  
Inverse Electron Demand ◽  
Lewis Acid Catalyst ◽  
Electron Demand

We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels–Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly enhancing its practicality. Comparative reactions were carried out to evaluate its catalytic activity in IEDDA reactions of diazine including phthalazine as well as 1,2,4,5-tetrazine.

Tandem inverse electron demand Diels–Alder, retro-Diels–Alder and intramolecular Diels–Alder sequences: one-pot synthesis of diaza-polycycles

Tetrahedron ◽  
2007 ◽  
Vol 63 (26) ◽  
pp. 6004-6014 ◽  
Author(s):  
William J. Bromley ◽  
Mairi Gibson ◽  
Stuart Lang ◽  
Steven A. Raw ◽  
Adrian C. Whitwood ◽  
...  
Keyword(s):  
Diels Alder ◽  
One Pot ◽  
Inverse Electron Demand ◽  
One Pot Synthesis ◽  
Electron Demand

The Coupling-Isomerization Approach to Enimines and the First Sequential Three-Component Access to 2-Ethoxy Pyridines

2004 ◽  
Vol 59 (4) ◽  
pp. 443-450 ◽  
Author(s):  
Oana G. Dediu ◽  
Nasser A. M. Yehia ◽  
Thomas J. J. Müller
Keyword(s):  
Diels Alder ◽  
Isomerization Reaction ◽  
One Pot ◽  
Inverse Electron Demand ◽  
Ketene Acetal ◽  
Electron Demand

AbstractThe coupling-isomerization reaction (CIR) of electron-deficient halides 1 with N-[1-(hetero)arylprop-2-ynyl] tosyl amides 2 leads to the formation of N-tosyl enimines 3, in good to excellent yields. These electron deficient heterodienes are perfectly suited for Diels-Alder reactions with inverse electron demand. In the sense of a one-pot reaction a three-component CIR-cyclocondensation sequence of 1, 2a, and diethyl ketene acetal gives rise to the formation of 2-ethoxy 6-(p-anisyl)pyridines 4 in moderate to good yields.

Recyclable Polymeric π-Acid Catalyst Effective in Aqueous and Solvent-Free Inverse-Electron-Demand Aza-Diels-Alder Reactions

Synlett ◽  
2006 ◽  
pp. 288-290 ◽  
Author(s):  
Yukio Masaki ◽  
Tomoyasu Yamada ◽  
Hyouei Kawai ◽  
Akichika Itoh ◽  
Yoshitsugu Arai ◽  
...  
Keyword(s):  
Acid Catalyst ◽  
Diels Alder ◽  
Solvent Free ◽  
Inverse Electron Demand ◽  
Electron Demand

Tandem Inverse Electron Demand Diels—Alder, Retro-Diels—Alder and Intramolecular Diels—Alder Sequences: One-Pot Synthesis of Diaza-Polycycles.

ChemInform ◽  
2007 ◽  
Vol 38 (42) ◽  
Author(s):  
William J. Bromley ◽  
Mairi Gibson ◽  
Stuart Lang ◽  
Steven A. Raw ◽  
Adrian C. Whitwood ◽  
...  
Keyword(s):  
Diels Alder ◽  
One Pot ◽  
Inverse Electron Demand ◽  
One Pot Synthesis ◽  
Electron Demand
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