scholarly journals Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

2020 ◽  
Vol 16 ◽  
pp. 691-737 ◽  
Author(s):  
Balaram S Takale ◽  
Ruchita R Thakore ◽  
Elham Etemadi-Davan ◽  
Bruce H Lipshutz
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Bond Forming Reactions

Numerous reactions generating C–Si and C–B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp3 carbon–silicon and carbon–boron bond-forming reactions are discussed.

Cu(III)-Mediated Aerobic Oxidations

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 334-358 ◽  
Author(s):  
Jean-Philip Lumb ◽  
Kenneth Esguerra
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Oxidation Reactions ◽  
General Introduction ◽  
Model Complexes ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Type 3

CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.1 General Introduction2 Early Examples of CuIII Complexes3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions5 Bioinorganic Studies of CuIII Complexes from CuI and O2 5.1 O2 Activation5.2 Biomimetic CuIII Complexes from CuI and Dioxygen5.2.1 Type-3 Copper Enzymes and Dinuclear Cu Model Complexes5.2.2 Particulate Methane Monooxygenase and Di- and Trinuclear Cu Model Complexes5.2.3 Dopamine–β-Monooxygenase and Mononuclear Cu Model Complexes6 Conclusion

scholarly journals Perfluorinated phosphine and hybrid P–O ligands for Pd catalysed C–C bond forming reactions in solution and on Teflon supports

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

Phosphine ligands containing a perfluorous ponytail can be sorbed onto Teflon tape and used as ligands for C–C cross coupling reactions with little leaching.

scholarly journals Biocatalytic oxidative cross-coupling reactions for biaryl bond formation

2021 ◽  
Author(s):  
Lara Zetzsche ◽  
Jessica Yazarians ◽  
Suman Chakrabarty ◽  
Meagan Hinze ◽  
April Lukowski ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Bond Formation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Cytochrome P450 Enzymes ◽  
Cross Coupling Reactions ◽  
Site Selectivity ◽  
Valuable Compounds ◽  
Selective Process

Despite their varied purposes, many indispensable molecules in medicine, materials, and asymmetric catalysis share a biaryl core. The necessity of joining arene building blocks to access these valuable compounds has inspired multiple approaches for biaryl bond formation and challenged chemists to develop increasingly concise and robust methods for this task. Oxidative coupling of two C–H bonds offers an efficient strategy for the formation of a biaryl C–C bond, however, fundamental challenges remain in controlling the reactivity and selectivity for uniting a given pair of substrates. Biocatalytic oxidative cross-coupling reactions have the potential to overcome limitations inherent to small molecule- mediated methods by providing a paradigm with catalyst-controlled selectivity. In this article, we disclose a strategy for biocatalytic cross-coupling through oxidative C–C bond formation using cytochrome P450 enzymes. We demonstrate the ability to catalyze cross-coupling reactions on a panel of phenolic substrates using natural P450 catalysts. Moreover, we engineer a P450 to possess the desired reactivity, site- selectivity, and atroposelectivity by transforming a low-yielding, unselective reaction into a highly efficient and selective process. This streamlined method for constructing sterically hindered biaryl bonds provides a programmable platform for assembling molecules with catalyst-controlled reactivity and selectivity.

Recent Advances in Enantioselective C–C Bond Formation via Organocobalt Species

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 135-145 ◽  
Author(s):  
Naohiko Yoshikai
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Bond Forming ◽  
Carbon Nucleophiles ◽  
Recent Advances ◽  
Catalytic Intermediates ◽  
Bond Forming Reactions ◽  
Recent Developments

This Short Review describes recent developments in cobalt-catalyzed enantioselective C–C bond-forming reactions. The article focuses on reactions that most likely involve chiral organocobalt species as crucial catalytic intermediates and their mechanistic aspects.1 Introduction2 Hydrovinylation3 C–H Functionalization4 Cycloaddition and Cyclization5 Addition of Carbon Nucleophiles6 Cross-Coupling7 Conclusion

Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 65-70 ◽  
Author(s):  
Paul Knochel ◽  
Maximilian Hofmayer ◽  
Jeffrey Hammann ◽  
Gérard Cahiez
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.

scholarly journals Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2293-2297 ◽  
Author(s):  
Allan Watson ◽  
Kirsty Wilson ◽  
Jane Murray ◽  
Helen Sneddon ◽  
Craig Jamieson
Keyword(s):  
Chemical Industry ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Heck Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Palladium-catalyzed bond-forming reactions, such as the ­Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).

Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)

Synlett ◽  
2021 ◽  
Author(s):  
Kenneth K. Laali ◽  
Rajesh G. Kalkhambkar ◽  
Suraj M. Sutar
Keyword(s):  
Ionic Liquids ◽  
Small Molecule ◽  
Biginelli Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Solvent Mixtures ◽  
Coupling Reactions ◽  
Ion Chemistry ◽  
Cross Coupling Reactions ◽  
Recent Advances

AbstractThe Account describes recent advances, from the authors’ laboratories, in the synthesis of diverse libraries of small-molecule building blocks employing ionic liquids (ILs). The ability of ILs to act as catalysts/promoters/solvents for electrophilic and onium ion chemistry, as well as in metal-mediated cross-coupling reactions, and the potential to sequence/hyphenate these methods, have opened up new opportunities for facile assembly of functional small molecules with increased complexity from readily available precursors. While Brønsted acidic IL/IL solvent mixtures are suitable media for carbocation and onium ion chemistry, piperidine-appended IL/IL solvent mixtures can successfully catalyze a variety of base-catalyzed reactions. Several widely practiced transformations including ‘name reactions’ were adapted and performed efficiently in ILs.1 Introduction2 Aryldiazonium Salts and Aryltriazenes as Coupling Partners in Metal-Mediated C–C Cross-Coupling Reactions in ILs3 Expanding the Scope of Metal-Mediated Cross-Coupling Reactions in ILs4 Application of ILs in Synthesis and Functionalization of Hetero­cycles5 Expanding the Scope of Amide Synthesis in ILs6 Generation and Chemistry of ‘Tamed’ Propargylic Cations in ILs7 Newer Nitration Methods for Arenes and Heteroarenes in ILs8 Halofunctionalization in ILs9 ‘Name Reactions’and Other Widely Practiced Synthetic Transformations in ILs9.1 The Biginelli Reaction9.2 Nitrile Synthesis by the Schmidt Reaction9.3 Rupe Rearrangement9.4 Synthesis of 1,3-Dioxanes via Prins Reaction in [BMIM(SO3H)][OTf]9.5 Synthesis of Cyclopropanes and Oxiranes by the Corey–Chaykovsky (CC) Reaction10 Conclusions and Closing Remarks

scholarly journals Sub-nanometre metal clusters for catalytic carbon–carbon and carbon–heteroatom cross-coupling reactions

2017 ◽  
Vol 46 (46) ◽  
pp. 15987-15990 ◽  
Author(s):  
A. Leyva-Pérez
Keyword(s):  
Metal Clusters ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

Potential new catalysts for C–C and C–Het cross-coupling bond-forming reactions.

Transition-metal-catalyzed carbon-carbon bond forming reactions: regio- and chemoselective iron(0)-catalyzed diene to olefin cross-coupling reactions

1986 ◽  
Vol 5 (11) ◽  
pp. 2395-2398 ◽  
Author(s):  
James M. Takacs ◽  
Lawrence G. Anderson ◽  
G. V. Bindu. Madhavan ◽  
Mark W. Creswell ◽  
Franklin L. Seely ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed
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