Cross coupling reactions overview

For overviews of applications of the Heck reaction in natural products synthesis, see (a) Link, J. T. Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions, Diederich, F., Stang, P. J., Eds. Wiley-VCH New York, 1998 Chapter 6. (b) Brase, S. de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions Diederich, F., Stang, P. J., Eds. Wiley New York, 1998 Chapter 3.6. (c) Nicolaou, K. C. Sorensen, E. J. Classics in Total Synthesis VCH New York, 1996 Chapter 31. These authors refer to the Heck reaction as "one of the true "power tools" of contemporary organic synthesis" (p. 566). 

As the vast area of cross-coupling reactions exceeds the coverage of this overview, more information can be found in a review by Jacobi von Wangelin covering the development in this field of chemistry up to 2008 [91]. 

Cross-coupling reactions 5-alkenylboron boron compounds, 9, 208 with alkenylpalladium(II) complexes, 8, 280 5-alkylboron boron, 9, 206 in alkyne C-H activations, 10, 157 5-alkynylboron compounds, 9, 212 5-allylboron compounds, 9, 212 allystannanes, 3, 840 for aryl and alkenyl ethers via copper catalysts, 10, 650 via palladium catalysts, 10, 654 5-arylboron boron compounds, 9, 208 with bis(alkoxide)titanium alkyne complexes, 4, 276 carbonyls and imines, 11, 66 in catalytic C-F activation, 1, 737, 1, 748 for C-C bond formation Cadiot-Chodkiewicz reaction, 11, 19 Hiyama reaction, 11, 23 Kumada-Tamao-Corriu reaction, 11, 20 via Migita-Kosugi-Stille reaction, 11, 12 Negishi coupling, 11, 27 overview, 11, 1-37 via Suzuki-Miyaura reaction, 11, 2 terminal alkyne reactions, 11, 15 for C-H activation, 10, 116-117 for C-N bonds via amination, 10, 706 diborons, 9, 167... 

Abstract N-heterocyclic carbenes (NHCs) have attracted increasing attention since their discovery. Notably, they have allowed for major advances in palladium-catalyzed reactions. Mainly known for their application in cross-coupling reactions, this review intends to provide a broader overview of (NHC)-palladium systems in organic transformations. 

Beilina F, Carpita A, Rossi R. Palladium catalysts for the Suzuki cross-coupling reaction an overview of recent advances. Synthesis 2004 2419-2440. 

Figure 1. Overview of metal-catalyzed C-C and C-N/C-0 cross-coupling reactions of halopyridines or C-metallated pyridines...

In recent years, these copper-catalyzed reactions have been studied intensively, and a large number of review articles on the copper-mediated formation of C-X (X = C, N, or O) bonds have appeared. This section of the chapter on cross-coupling provides an overview of the developments in copper-catalyzed coupling reactions. Mechanistic data on these reactions are far less extensive than those on cross-coupling reactions catalyzed... 

In this chapter, we attempt to provide a brief overview of the most developed synthetic methods to (ADC)Pd complexes and to systematize reports published until now on cross-coupling reactions catalyzed by (ADC)Pd systems. We also attempt to compare, whenever possible, the catalytic properties of (ADC)Pd versus (NHC)Pd species, and, eventually, to draw attention to the potential of ADCs and to the advantages that application of ADCs gives to the cross-coupling chemistry. 

Among the manifold variety of A-B molecules that can undergo oxidative addition, the ones possessing C-X bonds are typically involved in the oxidative addition step of cross-coupling reactions. Hence, since this thesis is focused on the theoretical study of these reactions catalyzed by Pd complexes, I found appropriate to include at the end of this section a brief overview of this type of oxidative additions. The aim of this overview is just to provide a general picture of which have been the main research interests related to this process, paying especial attention on the reported theoretical works. 

In this chapter, we attempt to provide an overview of the varying structures of suitable reaction partners in cross-couplings. Important recent developments and applications of the aforementioned reaction types will be discussed. 

CRM, see Cyclopentadienyl ring metathesis Cross-coupling polymerization miscellaneous reactions, 11, 678 overview, 11, 653-690... 

This review attempts to provide an overview of microwave-promoted metal-catalyzed transformations of aryl and vinyl halides (or pseudo halides), providing a personal selection of both pioneering and very recently published work. Covered areas include carbonylative transformations, Heck and Sono-gashira reactions, nucleophilic substitutions and cross-couplings. Because of the diversity of the microwave systems used, the reader should consult the original references for detailed descriptions of settings and instrumentation. 

---