Achieving Nickel Catalyzed C–S Cross-Coupling under Mild Conditions Using Metal–Ligand Cooperativity

2019 ◽  
Vol 84 (7) ◽  
pp. 4072-4085 ◽  
Author(s):  
Rina Sikari ◽  
Suman Sinha ◽  
Siuli Das ◽  
Anannya Saha ◽  
Gargi Chakraborty ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Metal Ligand

scholarly journals Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

2021 ◽  
Author(s):  
Travis DeLano ◽  
Sara Dibrell ◽  
Caitlin R. Lacker ◽  
Adam Pancoast ◽  
Kelsey Poremba ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

scholarly journals Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitro­styrenes

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2663-2676 ◽  
Author(s):  
Somayeh Motevalli ◽  
Jeffrey Johnson
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Coupling ◽  
Title Reaction ◽  
Dimethyl Phosphite ◽  
Mild Conditions ◽  
Michael Type Addition

A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate–phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

scholarly journals Pd–Ni Bimetallic Nanoparticles Supported on Zro2 as an Efficient Catalyst for Suzuki–Miyaura Reactions

2018 ◽  
Vol 42 (8) ◽  
pp. 419-423
Author(s):  
Li-Jie Zhang ◽  
Xian Yao ◽  
Ying-xin Sun ◽  
Jia-wei Zhang ◽  
Chun Cai
Keyword(s):  
Reduction Method ◽  
Bimetallic Nanoparticles ◽  
Bimetallic Catalyst ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Excellent Catalytic Performance

Pd–Ni bimetallic nanoparticles (BMNPs) supported on ZrO2 were prepared by an impregnation–reduction method. The BMNPs showed excellent catalytic performance in Suzuki carbon–carbon cross-coupling reactions and almost quantitative conversion of the substrates was obtained under mild conditions in the absence of ligand. The excellent catalytic performance of the bimetallic catalyst could be a result of the synergistic effect between the two metal components. The catalyst showed outstanding recyclability during the reaction process; no obvious decrease in catalytic performance was observed after five cycles.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles

Synthesis ◽  
2018 ◽  
Vol 50 (20) ◽  
pp. 3974-3996 ◽  
Author(s):  
Josep Cornella ◽  
Matthew O’Neill
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Chemical Space ◽  
Cross Coupling ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Substantial Progress ◽  
Tertiary Alkyl ◽  
Metal Ligand

While the advent of transition-metal catalysis has undoubtedly transformed synthetic chemistry, problems persist with the introduction of secondary and tertiary alkyl nucleophiles into C(sp2) aryl electrophiles. Complications arise from the delicate organometallic intermediates typically invoked by such processes, from which competition between the desired reductive elimination event and the deleterious β-H elimination pathways can lead to undesired isomerization of the incoming nucleophile. Several methods have integrated distinct combinations of metal, ligand, nucleophile, and electrophile to provide solutions to this problem. Despite substantial progress, refinements to current protocols will facilitate the realization of complement reactivity and improved functional group tolerance. These issues have become more pronounced in the context of green chemistry and sustainable catalysis, as well as by the current necessity to develop robust, reliable cross-couplings beyond less explored C(sp2)–C(sp2) constructs. Indeed, the methods discussed herein and the elaborations thereof enable an ‘unlocking’ of accessible topologically enriched chemical space, which is envisioned to influence various domains of application.1 Introduction2 Mechanistic Considerations3 Magnesium Nucleophiles4 Zinc Nucleophiles5 Boron Nucleophiles6 Other Nucleophiles7 Tertiary Nucleophiles8 Reductive Cross-Coupling with in situ Organometallic Formation9 Conclusion

scholarly journals A New Heterogeneous Catalyst Obtained via Supramolecular Decoration of Graphene with a Pd2+ Azamacrocyclic Complex

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2714 ◽  
Author(s):  
Matteo Savastano ◽  
Paloma Arranz-Mascarós ◽  
Maria Paz Clares ◽  
Rafael Cuesta ◽  
Maria Luz Godino-Salido ◽  
...  
Keyword(s):  
Heterogeneous Catalyst ◽  
Self Assembly ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Assembly Process ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Green Procedure

A new G-(H2L)-Pd heterogeneous catalyst has been prepared via a self-assembly process consisting in the spontaneous adsorption, in water at room temperature, of a macrocyclic H2L ligand on graphene (G) (G + H2L = G-(H2L)), followed by decoration of the macrocycle with Pd2+ ions (G-(H2L) + Pd2+ = G-(H2L)-Pd) under the same mild conditions. This supramolecular approach is a sustainable (green) procedure that preserves the special characteristics of graphene and furnishes an efficient catalyst for the Cu-free Sonogashira cross coupling reaction between iodobenzene and phenylacetylene. Indeed, G-(H2L)-Pd shows an excellent conversion (90%) of reactants into diphenylacetylene under mild conditions (50 °C, water, aerobic atmosphere, 14 h). The catalyst proved to be reusable for at least four cycles, although decreasing yields down to 50% were observed.

A highly efficient catalyst for Suzuki–Miyaura coupling reaction of benzyl chloride under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (69) ◽  
pp. 36437-36443 ◽  
Author(s):  
Zhenhong Guan ◽  
Buyi Li ◽  
Guoliang Hai ◽  
Xinjia Yang ◽  
Tao Li ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Benzyl Chloride ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Microporous Polymers ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reactions

Microporous polymers with built-in triphenylphosphine palladium exhibit highly efficient catalytic activity for cross-coupling reactions of benzyl chloride under mild conditions.

Ligand-Free Nickel-Catalyzed Reductive Allylic Defluorinative Cross-Coupling of α-Trifluoromethyl Alkenes with Epoxides

Synlett ◽  
2020 ◽  
Author(s):  
Chuan Wang ◽  
Zhiyang Lin ◽  
Yun Lan
Keyword(s):  
Ring Opening ◽  
Cross Coupling ◽  
Proton Donor ◽  
Mild Conditions ◽  
Ligand Free ◽  
High Yields ◽  
Radical Type

We report a reductive allylic defluorinative reaction of α-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gem-difluorobishomoallylic alcohols in moderate to high yields. Notably, this reaction is conducted under mild conditions and requires no external ligand or proton donor.

(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki–Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 799-804 ◽  
Author(s):  
Mark Stradiotto ◽  
Ryan Sawatzky
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Mild Conditions

The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki–Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.

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