1,1-Disubstituted olefin synthesis via Ni-catalyzed Markovnikov hydroalkylation of alkynes with alkyl halides

2016 ◽  
Vol 52 (30) ◽  
pp. 5324-5327 ◽  
Author(s):  
Xiao-Yu Lu ◽  
Jing-Hui Liu ◽  
Xi Lu ◽  
Zheng-Qi Zhang ◽  
Tian-Jun Gong ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Olefin Synthesis

A Ni-catalyzed Markovnikov hydroalkylation of alkynes with alkyl halides is described.

Trisubstituted olefin synthesis via Ni-catalyzed hydroalkylation of internal alkynes with non-activated alkyl halides

2018 ◽  
Vol 54 (35) ◽  
pp. 4417-4420 ◽  
Author(s):  
Xiao-Yu Lu ◽  
Mei-Lan Hong ◽  
Hai-Pin Zhou ◽  
Yue Wang ◽  
Jin-Yu Wang ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Alkyl Halides ◽  
Olefin Synthesis ◽  
Internal Alkynes

The stereoselective synthesis of tri-substituted alkenes is challenging.

scholarly journals Regio- and stereoselective multisubstituted olefin synthesis via hydro/carboalumination of alkynes and subsequent iron-catalysed cross-coupling reaction with alkyl halides

2015 ◽  
Vol 2 (9) ◽  
pp. 1053-1058 ◽  
Author(s):  
Shintaro Kawamura ◽  
Ryosuke Agata ◽  
Masaharu Nakamura
Keyword(s):  
Iron Catalyst ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Synthetic Route ◽  
Olefin Synthesis ◽  
Cross Coupling Reaction ◽  
Direct Cross

A new synthetic route towards multisubstituted olefins was developed based on the direct cross coupling of alkenyl aluminium reagents, prepared by hydro- and carboalumination, with alkyl halides in the presence of an iron catalyst.

ChemInform Abstract: 1,1-Disubstituted Olefin Synthesis via Ni-Catalyzed Markovnikov Hydroalkylation of Alkynes with Alkyl Halides.

ChemInform ◽  
2016 ◽  
Vol 47 (33) ◽  
Author(s):  
Xiao-Yu Lu ◽  
Jing-Hui Liu ◽  
Xi Lu ◽  
Zheng-Qi Zhang ◽  
Tian-Jun Gong ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Olefin Synthesis

Vitamin B12-based elimination of alkyl halides

2020 ◽  
Author(s):  
Julian West ◽  
Alexandros S Pollatos ◽  
Radha Bam
Keyword(s):  
Vitamin B12 ◽  
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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