scholarly journals Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions

2018 ◽  
Vol 9 (8) ◽  
pp. 2195-2211 ◽  
Author(s):  
Takanori Iwasaki ◽  
Asuka Fukuoka ◽  
Wataru Yokoyama ◽  
Xin Min ◽  
Ichiro Hisaki ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Theoretical Methods ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Detailed Reaction Mechanism

The detailed reaction mechanism of anionic Ni complex-promoted C–C bond forming reactions was clarified by experimental and theoretical methods.

Iron-Catalysedsp3–sp3 Cross-Coupling Reactions of Unactivated Alkyl Halides with Alkyl Grignard Reagents

2007 ◽  
Vol 349 (7) ◽  
pp. 1015-1018 ◽  
Author(s):  
Krishna G. Dongol ◽  
Huishi Koh ◽  
Manisankar Sau ◽  
Christina L. L. Chai
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 65-70 ◽  
Author(s):  
Paul Knochel ◽  
Maximilian Hofmayer ◽  
Jeffrey Hammann ◽  
Gérard Cahiez
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.

scholarly journals Cross‐Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents Using a Tetrachloroferrate with an Innocent Countercation

2019 ◽  
Vol 361 (18) ◽  
pp. 4232-4236 ◽  
Author(s):  
Toru Hashimoto ◽  
Tsubasa Maruyama ◽  
Takamichi Yamaguchi ◽  
Yutaka Matsubara ◽  
Yoshitaka Yamaguchi
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

On direct iron-catalyzed cross-coupling reactions

2010 ◽  
Vol 82 (7) ◽  
pp. 1545-1553 ◽  
Author(s):  
Waldemar Maximilian Czaplik ◽  
Matthias Mayer ◽  
Sabine Grupe ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross

A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.

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