Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions

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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Nickel and Cobalt-Catalyzed Coupling of Alkyl Halides with Alkenes via Heck Reactions and Radical Conjugate Addition

Mini-Reviews in Medicinal Chemistry ◽

10.2174/1389557511313060003 ◽

2013 ◽

Vol 13 (6) ◽

pp. 802-813 ◽

Cited By ~ 17

Author(s):

Qun Qian ◽

Zhenhua Zang ◽

Yang Chen ◽

Weiqi Tong ◽

Hegui Gong

Keyword(s):

Conjugate Addition ◽

Alkyl Halides ◽

Heck Reactions

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Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽

10.1055/s-0040-1707229 ◽

2020 ◽

Vol 52 (22) ◽

pp. 3466-3472

Author(s):

Yunkui Liu ◽

Bingwei Zhou ◽

Qiao Li ◽

Hongwei Jin

Keyword(s):

Functional Group ◽

Coupling Reaction ◽

Alkyl Halides ◽

Previous Literature ◽

Catalytic Cycle ◽

Reaction Conditions ◽

Multicomponent Coupling ◽

Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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ChemInform Abstract: ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE-CONTAINING COMPLEX REDUCING AGENTS. 16. FECRACO, A NEW REAGENT FOR THE CARBONYLATION OF PRIMARY, SECONDARY, AND TERTIARY ALKYL HALIDES AT ATMOSPHERIC PRESSURE

Chemischer Informationsdienst ◽

10.1002/chin.198149138 ◽

1981 ◽

Vol 12 (49) ◽

Author(s):

J.-J. BRUNET ◽

C. SIDOT ◽

P. CAUBERE

Keyword(s):

Atmospheric Pressure ◽

Sodium Hydride ◽

Reducing Agents ◽

Alkyl Halides ◽

Tertiary Alkyl

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Facile reaction of o-carboranyllithium reagents with functionalized alkyl halides

Tetrahedron Letters ◽

10.1016/0040-4039(96)00552-7 ◽

1996 ◽

Vol 37 (19) ◽

pp. 3383-3386 ◽

Cited By ~ 9

Author(s):

Jianping Cai ◽

Hiaso Nemoto ◽

Bakthan Singaram ◽

Yoshinori Yamamoto

Keyword(s):

Alkyl Halides

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Synthesis of sandwich type acyclic tetra-nuclear silver(I)-N-heterocyclic carbene complexes for wound healing applications

Zeitschrift für Naturforschung C ◽

10.1515/znc-2020-0069 ◽

2020 ◽

Vol 75 (9-10) ◽

pp. 369-376

Author(s):

Ayesha Riaz ◽

Muhammad Adnan Iqbal ◽

Haq Nawaz Bhatti ◽

Muhammad Shahid

Keyword(s):

Alkyl Halides ◽

Wound Contraction ◽

Spectroscopic Techniques ◽

Open Chain ◽

Standard Drug ◽

Sandwich Type ◽

Benzimidazolium Salts ◽

Multistep Reaction

AbstractTwo meta-xylyl linked tetrakis-benzimidazolium salts (L1-L2) as multidentate ligands and two respective silver complexes (C1 and C2) were synthesized. A multistep reaction was done at room temperature, starting with simple benzimidazole and alkyl halides, going through precursors and salt formation by reflux and finally in situ deprotonation of tetrabenzimidazolium salts with Ag2O to yield respective tetra-nuclear Ag(I)-N-heterocyclic Carbene (NHC) complexes. Propyl and butyl groups were bonded at the terminal positions of tetra-azolium open chain salts. Characterization of compounds was done by analytical and spectroscopic techniques. On the basis of spectroscopic data, a chemical structure with open chains having four Ag(I) ions sandwiched between NHC layers was established. Potential of synthesized complexes (C1 & C2) for wound contraction was evaluated and compared with standard wound contraction gel. Percentage wound contraction of both complexes was found very close to that of standard drug used in parallel.

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