Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides

2018 ◽  
Vol 140 (49) ◽  
pp. 16929-16935 ◽  
Author(s):  
Chunlin Tang ◽  
Ran Zhang ◽  
Bo Zhu ◽  
Junkai Fu ◽  
Yi Deng ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Type Reaction

Cobalt-Catalyzed Heck-Type Reaction of Alkyl Halides with Styrenes

2002 ◽  
Vol 124 (23) ◽  
pp. 6514-6515 ◽  
Author(s):  
Yousuke Ikeda ◽  
Tomoaki Nakamura ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Alkyl Halides ◽  
Type Reaction

ChemInform Abstract: Cobalt-Catalyzed Heck-Type Reaction of Alkyl Halides with Styrenes.

ChemInform ◽  
2010 ◽  
Vol 33 (42) ◽  
pp. no-no
Author(s):  
Yousuke Ikeda ◽  
Tomoaki Nakamura ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Alkyl Halides ◽  
Type Reaction

Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α-(Trifluoromethyl)styrenes

2021 ◽  
Author(s):  
Anton A. Gladkov ◽  
Grigory N. Chernov ◽  
Vitalij V. Levin ◽  
Vladimir A. Kokorekin ◽  
Alexander D. Dilman
Keyword(s):  
Alkyl Halides ◽  
Type Reaction ◽  
Organozinc Reagents

Vitamin B12-based elimination of alkyl halides

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

Cerium-catalyzed reformatsky-type reaction with ethyl bromosuccinate for the synthesis of γ-lactones

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
S Muniz Machado Rodrigues ◽  
GVJ da Silva ◽  
M Gomes Constantino
Keyword(s):  
Type Reaction

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.

Sign in / Sign up

Export Citation Format

Share Document