Microwave-assisted C–C bond forming cross-coupling reactions: an overview

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

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Cu(III)-Mediated Aerobic Oxidations

Synthesis ◽

10.1055/s-0037-1609635 ◽

2018 ◽

Vol 51 (02) ◽

pp. 334-358 ◽

Cited By ~ 9

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

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Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

Chemistry of Heterocyclic Compounds ◽

10.1007/s10593-015-1732-3 ◽

2015 ◽

Vol 51 (6) ◽

pp. 563-567 ◽

Cited By ~ 3

Author(s):

Gulnihan Onar ◽

Mert Olgun Karatas ◽

Bülent Alici ◽

Engin Cetinkaya

Keyword(s):

Cross Coupling ◽

Microwave Assisted Synthesis ◽

Coupling Reactions ◽

Microwave Assisted ◽

Cross Coupling Reactions ◽

Palladium Catalyzed

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

RSC Advances ◽

10.1039/c9ra04863d ◽

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.

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