FACTORS INFLUENCING THE COURSE AND MECHANISM OF GRIGNARD REACTIONS. XIX. THE PREPARATION OF SUBSTITUTED BIBENZYLS FROM GRIGNARD REAGENTS, ALKYL HALIDES, AND ALKYLBENZENES, IN THE PRESENCE AND ABSENCE OF COLBALTOUS CHLORIDE

1948 ◽  
Vol 13 (1) ◽  
pp. 101-109 ◽  
Author(s):  
M. S. KHARASCH ◽  
W. H. URRY
Keyword(s):  
Alkyl Halides ◽  
Grignard Reagents ◽  
Factors Influencing ◽  
Grignard Reactions ◽  
Presence And Absence

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Mechanism of formation of Grignard reagents. Kinetics of reaction of alkyl halides in diethyl ether with magnesium

1980 ◽  
Vol 102 (1) ◽  
pp. 217-226 ◽  
Author(s):  
Harold R. Rogers ◽  
Craig L. Hill ◽  
Yuzo Fujiwara ◽  
Randall J. Rogers ◽  
H. Lee Mitchell ◽  
...  
Keyword(s):  
Diethyl Ether ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanism Of Formation ◽  
Kinetics Of Reaction ◽  
Kinetics Of

Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents

2004 ◽  
Vol 126 (12) ◽  
pp. 3686-3687 ◽  
Author(s):  
Masaharu Nakamura ◽  
Keiko Matsuo ◽  
Shingo Ito ◽  
Eiichi Nakamura
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents
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