Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides with Alkyl Carboxylic Acids

2021 ◽  
Author(s):  
Ke-Jin Jiao ◽  
Cong Ma ◽  
Dong Liu ◽  
Hui Qiu ◽  
Bin Cheng ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Undivided Cell ◽  
Alkyl Bromides ◽  
Direct Acylation

A highly regioselective Ni-catalyzed electrochemical (undivided cell) reductive relay cross-coupling between alkyl carbox-ylic acids and alkyl bromides has been developed. This strategy allows the direct acylation of benzylic C(sp3)–H bonds...

ChemInform Abstract: Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives.

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives

2013 ◽  
Vol 78 (21) ◽  
pp. 10642-10650 ◽  
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

scholarly journals Metallaphotoredox-catalysed sp3–sp3 cross-coupling of carboxylic acids with alkyl halides

Nature ◽  
2016 ◽  
Vol 536 (7616) ◽  
pp. 322-325 ◽  
Author(s):  
Craig P. Johnston ◽  
Russell T. Smith ◽  
Simon Allmendinger ◽  
David W. C. MacMillan
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Alkyl Halides

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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