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

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Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.

C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals

This Review covers recent progress on near-infrared fluorescence imaging for preclinical animal studies and clinical diagnostics and interventions.

Near-infrared fluorophores for biomedical imaging

Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aube rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

The reaction generates a C—C double bond in a very efficient manner with only AcOH as the side product.

A General Protocol for the Solvent- and Catalyst-Free Synthesis of 2-Styrylquinolines under Focused Microwave Irradiation.

Solid-state synthetic chemistry has some potential advantages that include the absence of solubility issues and solvation phenomena, together with increased environmental friendliness. Mechanochemical synthesis, in particular, has undergone an exponential growth in recent years and has led to the improvement of many previously known transformations and the development of new ones. This chapter is aimed at providing a critical outlook of these developments.

Solid-State Green Organic Reactions

The biologically important heterocyclic skeleton is formed with complete diastereoselectivity but in a nearly racemic form despite the presence of an optically active catalyst.

L-Proline-Catalyzed Three-Component Domino Reactions for the Diastereoselective Synthesis of 5,6-Disubstituted 3-Thiomorpholinones.

1-Allyl(propargyl)-6-allyl(propargyl)oxy-1,4,5,6-tetrahydropyridines, obtained through a CAN-catalyzed four-component reaction, were transformed into highly functionalized pyrido[2,1-b][1,3]oxazepines by ring-closing metathesis (RCM) and ring-closing enyne metathesis (RCEYM) processes, which constitute the first examples of the preparation of 1,3-oxazepine systems using metathesis reactions.

Efficient Generation of Highly Functionalized Fused Oxazepine Frameworks Based on a CAN‐Catalyzed Four‐Component Tetrahydropyridine Synthesis/Ring‐Closing Metathesis Sequence.

New 2-pyrrolin-5-ones (IV) are prepared by Hantzsch—type microwave-assisted, solvent-free sequential three-component reaction of primary amines, β-carbonyl compounds, and α-bromoester and utilized e.g. as synthetic building blocks in a target-oriented project for the synthesis of compound (VI) that is postulated as a candidate for HIV increase inhibition on the basis of computational studies.

J. Carlos Menéndez

Papers

A General Protocol for the Solvent- and Catalyst-Free Synthesis of 2-Styrylquinolines under Focused Microwave Irradiation.

Solid-State Green Organic Reactions

L-Proline-Catalyzed Three-Component Domino Reactions for the Diastereoselective Synthesis of 5,6-Disubstituted 3-Thiomorpholinones.

Efficient Generation of Highly Functionalized Fused Oxazepine Frameworks Based on a CAN‐Catalyzed Four‐Component Tetrahydropyridine Synthesis/Ring‐Closing Metathesis Sequence.

Three‐Component Access to 2‐Pyrrolin‐5‐ones and Their Use in Target‐Oriented and Diversity‐Oriented Synthesis.