ChemInform Abstract: Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides.

Carbon dioxide is not only an essential component of ‘greenhouse gases’, but also an abundant, renewable C1 feedstock in organic synthesis. The catalytic incorporation of carbon dioxide into value-added chemicals to produce carboxylic acids has received enormous attention. This review summarizes recent developments in the transition-metal-catalyzed carboxylation of organic halides and their surrogates, such as aryl, vinyl, and alkyl halides and pseudohalides.1 Introduction2 Carboxylation of Aryl Halides and Pseudohalides3 Carboxylation of Vinyl Halides and Pseudohalides4 Carboxylation of Benzyl Halides and Pseudohalides5 Carboxylation of Allyl Halides and Pseudohalides6 Carboxylation of Propargyl Halides and Pseudohalides7 Carboxylation of Alkyl Halides and Pseudohalides8 Direct Carboxylation of C–H Bonds9 Conclusions and Perspectives

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Photochemistry of alkyl halides. 10. Vinyl halides and vinylidene dihalides

Journal of the American Chemical Society ◽

10.1021/ja00361a028 ◽

1983 ◽

Vol 105 (23) ◽

pp. 6907-6915 ◽

Cited By ~ 47

Author(s):

Paul J. Kropp ◽

Steven A. McNeely ◽

Robert Drummond Davis

Keyword(s):

Alkyl Halides ◽

Vinyl Halides

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ChemInform Abstract: PHOTOCHEMISTRY OF ALKYL HALIDES. 10. VINYL HALIDES AND VINYLIDENE DIHALIDES

Chemischer Informationsdienst ◽

10.1002/chin.198408084 ◽

1984 ◽

Vol 15 (8) ◽

Author(s):

P. J. KROPP ◽

S. A. MCNEELY ◽

R. D. DAVIS

Keyword(s):

Alkyl Halides ◽

Vinyl Halides

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Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides

Chemistry - A European Journal ◽

10.1002/chem.201601320 ◽

2016 ◽

Vol 22 (22) ◽

pp. 7399-7402 ◽

Cited By ~ 44

Author(s):

Keywan A. Johnson ◽

Soumik Biswas ◽

Daniel J. Weix

Keyword(s):

Alkyl Halides ◽

Vinyl Halides

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Vitamin B12-based elimination of alkyl halides

10.1021/scimeetings.0c06697 ◽

2020 ◽

Author(s):

Julian West ◽

Alexandros S Pollatos ◽

Radha Bam

Keyword(s):

Vitamin B12 ◽

Alkyl Halides

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

10.26434/chemrxiv.12049377.v1 ◽

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.

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

10.26434/chemrxiv.9858500.v1 ◽

2019 ◽

Cited By ~ 1

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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