ChemInform Abstract: Nickel-Catalyzed Cross-Coupling of Sterically Hindered 1-Bromomethyl-o-carborane with Alkyl and Aryl Grignard Reagents

ChemInform ◽  
2015 ◽  
Vol 46 (44) ◽  
pp. no-no
Author(s):  
Juyou Lu ◽  
Hong Wan ◽  
Yunna Xue ◽  
Yongmei Du ◽  
Jian Lu
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Sterically Hindered

scholarly journals Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers

2018 ◽  
Vol 8 (1) ◽  
pp. 328-334 ◽  
Author(s):  
Gavin J. Harkness ◽  
Matthew L. Clarke
Keyword(s):  
Nickel Complexes ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Sterically Hindered

The challenging reaction of unactivated ortho-substituted aromatic ethers with Grignard reagents has been found to be most effectively catalysed using nickel complexes of less sterically hindered ligands.

Nickel-catalyzed cross-coupling of sterically hindered 1-bromomethyl-o-carborane with alkyl and aryl Grignard reagents

Tetrahedron ◽  
2015 ◽  
Vol 71 (41) ◽  
pp. 7842-7846 ◽  
Author(s):  
Juyou Lu ◽  
Hong Wan ◽  
Yunna Xue ◽  
Yongmei Du ◽  
Jian Lu
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Sterically Hindered

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.

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