Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

6.4. Polyynes 3123 6.5. Using R-Hydroxy Stannanes 3124 6.6. Using the Hurtley Reaction 3124 6.7. Using a Methylenation Reaction 3125 7. Conclusions and Future Prospects 3125 8. Uncommon Abbreviations 3125 9. Acknowledgments 3125 10. Note Added in Proof 3125 11. References 3126 * Authorstowhomcorrespondenceshouldbeaddressed(evano@chimie.uvsq.fr, nicolas.blanchard@uha.fr). † Université de Versailles Saint Quentin en Yvelines. ‡ Université de Haute-Alsace. Chem. Rev. 2008, 108, 3054–3131 3054

Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Direct C-H transformation via iron catalysis.

Amide bond formation is a fundamentally important reaction in organic synthesis, and is typically mediated by one of a myriad of so-called coupling reagents. This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of “acronym” based reagents. It aims to demystify the process allowing the chemist to make a sensible and educated choice when carrying out an amide coupling reaction (179 references).

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Organicka%20chemia%20II/Prednaska%208_Aminokyseliny%20a%20peptidy/Doplnkove%20studijne%20materialy/Amide%20bond%20formation/Amide%20bond%20formation%20-%20beyond%20the%20myth%20of%20coupling%20reagents.pdf

Amide bond formation: beyond the myth of coupling reagents

3.1. C-M and X-H as Nucleophiles 1806 3.2. C-H and X-M as Nucleophiles 1809 3.2.1. C-Halogen Bond Formations 1809 3.2.2. C-O Bond Formations 1812 3.3. C-H and X-H as Nucleophiles 1812 3.3.1. C-O Bond Formations 1812 3.3.2. C-N Bond Formations 1815 4. Oxidative X-X Bond Formations between Two Nucleophiles 1819 5. Conclusions 1819 Author Information 1819 Biographies 1819 Acknowledgment 1820 References 1820

Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions

A new and readily available bidentate ligand, namely, pyrrolidine-2-phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.

A Versatile and Efficient Ligand for Copper‐Catalyzed Formation of C ? N, C ? O, and P ? C Bonds: Pyrrolidine‐2‐Phosphonic Acid Phenyl Monoester

A Simple and Efficient Approach to Quinazolinones under Mild Copper‐Catalyzed Conditions

A simple and general copper-catalyzed method has been developed for transformations of various functional groups (-I, -N(3), -SO(2)R, -OH, -NH(2), and -NO(2)) on aromatic rings from arylboronic acids in water under air. The protocol uses cheap and readily available inorganic salts (KI, NaN(3), NaSO(2)R, NaOH, NaNO(2)) and aqueous ammonia as the functional-group sources, simple Cu(2)O/NH(3) as the catalyst system, environmentally friendly water as the solvent, and oxygen in air as the oxidant. Importantly, the copper catalyst system in water was recyclable. This study should provide a useful strategy for interconversions of the functional groups on aromatic rings.

Hua Fu

Papers

A Versatile and Efficient Ligand for Copper‐Catalyzed Formation of C ? N, C ? O, and P ? C Bonds: Pyrrolidine‐2‐Phosphonic Acid Phenyl Monoester

A Simple and Efficient Approach to Quinazolinones under Mild Copper‐Catalyzed Conditions

General Copper‐Catalyzed Transformations of Functional Groups from Arylboronic Acids in Water

Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives.

Efficient intermolecular iron-catalyzed amidation of C-H bonds in the presence of N-bromosuccinimide