Recent progress and current applications of Sonogashira coupling reaction in water

Abstract

The use of aqueous media in palladium‐catalyzed reactions has become popular because water‐based synthetic processes are inherently safer as well as being inexpensive. Moreover, it does not require dry solvents, and the products may easily be isolated by extraction, which greatly facilitates the operation. Thus the use of water in palladium‐catalyzed reactions represents one of the most economically and environmentally viable options for many organic transformations. In this review, recent developments of Sonogashira reaction in water or aqueous media will be disclosed. Copyright © 2013 John Wiley & Sons, Ltd.

Synthesis and Transformation of Halochromones

“…Subsequently, the proximity of the carbon atoms bound to the metal assists in their coupling with the formation of a new carbon-carbon single bond. This powerful synthetic methodology [147][148][149][150][151] is considered a golden strategic tool to build novel complex molecules, which have promising bioactive properties [152]. The awarding of the 2010 Nobel Prize in Chemistry to R. F. Heck, E. Negishi, and A. Suzuki, gave even more the attention to the development of these reactions [153,154].…”

Efficient and green catalytic system incorporating new benzimidazolium salts for the Sonogashira cross‐coupling reaction

“…Today, the Sonogashira coupling reaction is known as a powerful method for the synthesis of novel alkynes derived from terminal acetylenes and aryl or vinyl halides. [2][3][4][5][6][7][8][9][10][11] Although palladiumphosphine complexes and copper-based catalysts have been mostly used in the Sonogashira reaction, the addition of copper(I) salts as co-catalysts has some drawbacks such as Glaser-type homocoupling and phosphine-based ligands causing environmental pollution. [2] In order to prevent these unwanted effects, many researchers have also tried copper-free and metal-free Sonogashira reaction protocols.…”

“…[2] In order to prevent these unwanted effects, many researchers have also tried copper-free and metal-free Sonogashira reaction protocols. [4,[12][13][14][15][16][17][18][19] Many of these methods involve long reaction times and low reaction yields. After the isolation of stable N-heterocyclic carbenes by Arduengo and co-workers in 1991, a new window was opened for scientists who worked on metal-mediated catalytic syntheses due to the ease of synthesis of N-heterocyclic carbene ligands which have better σ-donor ability, lower toxicity and better thermal stability than phosphine-based ligands.…”

A Doubly Alkynylpyrene‐Threaded [4]Rotaxane That Exhibits Strong Circularly Polarized Luminescence from the Spatially Restricted Excimer

“…Unfortunately, formation of an amide bond between the terminal amino groups in 1 a and the carboxy groups of various stopper molecules failed. After exhaustive attempts, we finally succeeded in forming a rotaxane through Sonogashira coupling [14] between the newly synthesized acetylene-terminated alkynylpyrene 1 b [15] and 4,4''-biscarboxy-5'-iodo-1,1':3',1''-terphenyl (2) [16] in water ( Figure 2). A mixture of 1 b, 2, palladium catalyst, and g-CD was stirred for 72 h at 30 8C, acidified, and filtered.…”