Oxazolines. 3. Regioselective synthesis of 2-(monosubstituted phenyl) and/or unsymmetrically 2-(disubstituted phenyl) 2-oxazolines by cross-coupling Grignard reagents to (haloaryl)-2-oxazolines

1982 ◽  
Vol 47 (22) ◽  
pp. 4319-4323 ◽  
Author(s):  
Lendon N. Pridgen
Keyword(s):  
Cross Coupling ◽  
Regioselective Synthesis ◽  
Grignard Reagents

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.

Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system

2012 ◽  
Vol 53 (28) ◽  
pp. 3556-3559 ◽  
Author(s):  
Marcio S. Silva ◽  
Renan S. Ferrarini ◽  
Bruno A. Sousa ◽  
Fabiano T. Toledo ◽  
João V. Comasseto ◽  
...  
Keyword(s):  
Catalytic System ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions
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