The First Nucleophilic Aromatic Substitution of Suitably Activated 2-Methoxyfurans with Grignard Reagents.

ChemInform ◽  
2003 ◽  
Vol 34 (46) ◽  
Author(s):  
M. Rosaria Iesce ◽  
M. Liliana Graziano ◽  
Flavio Cermola ◽  
Stefania Montella ◽  
Lucrezia Di Gioia
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Grignard Reagents ◽  
Aromatic Substitution

The first nucleophilic aromatic substitution of suitably activated 2-methoxyfurans with Grignard reagents

2003 ◽  
Vol 44 (31) ◽  
pp. 5781-5784 ◽  
Author(s):  
M.Rosaria Iesce ◽  
M.Liliana Graziano ◽  
Flavio Cermola ◽  
Stefania Montella ◽  
Lucrezia Di Gioia
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Grignard Reagents ◽  
Aromatic Substitution

scholarly journals Icosahedral Meta-Carboranes Containing Exopolyhedral B-Se and B-Te Bonds

2021 ◽  
Author(s):  
Harrison Mills ◽  
Fadi Alsarhan ◽  
Ta-Chung Ong ◽  
Milan Gembicky ◽  
Arnold Rheingold ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Nucleophilic Aromatic Substitution ◽  
Grignard Reagents ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Reactivity Pattern ◽  
Electrophilic Reactions ◽  
Substitution Chemistry ◽  
Electrophilic Reactivity

Chalcogen-containing carboranes have been known for several decades and possess stable exopolyhedral B(9)-Se and B(9)-Te σ bonds despite the electron-donating ability of the B(9) vertex. While these molecules are known, little has been done to thoroughly evaluate their electrophilic and nucleophilic behavior. Herein, we report an assessment of the electrophilic reactivity of meta-carboranyl selenyl (II), tellurenyl (II), and tellurenyl (IV) chlorides and establish their reactivity pattern with Grignard reagents, alkenes, alkynes, enolates, and electron-rich arenes. These electrophilic reactions afford unique electron-rich B-Y-C (Y = Se, Te) bonding motifs not commonly found before. Furthermore, we show that meta-carboranyl selenolate, and even meta-carboranyl tellurolate, can be competent nucleophiles and participate in nucleophilic aromatic substitution reactions. Arene substitution chemistry is shown to be further extended to electron-rich species via the palladium mediated cross-coupling chemistry.

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