Aspects of the metallic halide-catalysed reaction of Grignard reagents with organic halides. Part III. Reactions with bromopyridines

1969 ◽  
pp. 2019 ◽  
Author(s):  
D. I. Davies ◽  
J. N. Done ◽  
D. H. Hey
Keyword(s):  
Grignard Reagents ◽  
Catalysed Reaction ◽  
Organic Halides

Chromium-Catalyzed, Regioselective Cross-Coupling of C–O Bonds by Using Organic Bromides as Reactants

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2577-2580 ◽  
Author(s):  
Meiming Luo ◽  
Xiaoming Zeng ◽  
Jinghua Tang
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Aromatic Aldehydes ◽  
Grignard Reagents ◽  
Metallic Magnesium ◽  
Organic Halides

We report a chromium-catalyzed cross-coupling of C–O bonds with widely accessible organic bromides as reactants for the preparation of ortho-arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

Recent Advances in Magnesium Carbenoid Chemistry

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5105-5119 ◽  
Author(s):  
Tsutomu Kimura
Keyword(s):  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Short Review ◽  
Grignard Reagents ◽  
Nucleophilic Reactions ◽  
Recent Advances ◽  
Electrophilic Reactions ◽  
Organic Halides ◽  
Reactions With Nucleophiles

Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures of Magnesium Carbenoids3 Reactions of Magnesium Carbenoids as Nucleophiles3.1 Nucleophilic Reactions of Magnesium Carbenoids3.2 Nucleophilic Reactions of Magnesium Alkylidene Carbenoids3.3 Nucleophilic Reactions of Cyclopropylmagnesium Carbenoids4 Electrophilic Reactions of Magnesium Carbenoids4.1 Reactions with Nucleophiles Followed by Electrophiles4.2 Reactions with Nucleophiles Possessing Electrophilic Functional Groups4.3 Nucleophilic Substitution Followed by β-Elimination5 Rearrangements of Magnesium Carbenoids5.1 1,2-Shifts of Magnesium Carbenoids5.2 1,3-C–H Insertions of Magnesium Carbenoids5.3 1,5-C–H Insertions of Magnesium Carbenoids5.4 [2+1] Cycloaddition of a Magnesium Carbenoid6 Conclusion and Outlook

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