Nickel-Catalyzed Defluorinative Reductive Cross-Coupling of gem-Difluoroalkenes with Unactivated Secondary and Tertiary Alkyl Halides

2017 ◽  
Vol 139 (36) ◽  
pp. 12632-12637 ◽  
Author(s):  
Xi Lu ◽  
Yan Wang ◽  
Ben Zhang ◽  
Jing-Jing Pi ◽  
Xiao-Xu Wang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Tertiary Alkyl

ChemInform Abstract: Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive.

ChemInform ◽  
2013 ◽  
Vol 44 (50) ◽  
pp. no-no
Author(s):  
Takanori Iwasaki ◽  
Hiroaki Takagawa ◽  
Surya P. Singh ◽  
Hitoshi Kuniyasu ◽  
Nobuaki Kambe
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Tertiary Alkyl

scholarly journals Direct C(sp2)C(sp3) Cross-Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

2015 ◽  
Vol 127 (19) ◽  
pp. 5780-5784 ◽  
Author(s):  
Jay J. Dunsford ◽  
Ewan R. Clark ◽  
Michael J. Ingleson
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Tertiary Alkyl

Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive

2013 ◽  
Vol 135 (26) ◽  
pp. 9604-9607 ◽  
Author(s):  
Takanori Iwasaki ◽  
Hiroaki Takagawa ◽  
Surya P. Singh ◽  
Hitoshi Kuniyasu ◽  
Nobuaki Kambe
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Tertiary Alkyl

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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