Coupling reactions in organic synthesis

Kotha S, Lahiri S, Kashinath D (2002) Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis. Tetrahedron 58 9633-9695... 

The following Pd-catalyzed organometallic C-C coupling reaction [1-3] is an important coupling reaction in organic synthesis [4-7]. 

S. Kotha, K. Lahiri, D. Kashinath, Recent Applications of the Suzuki-Miyaura Cross-Coupling Reaction in Organic Synthesis, Tetrahedron 2002, 58, 9633-9695. 

Toumi, M., Gouty, F. and Evano, G. (2007) Total synthesis of the cyclopeptide alkaloid abyssenine A. Application of inter- and intramolecular copper-mediated coupling reactions in organic synthesis. The Journal of Organic Chemistry, 72, 9003-9009. 

Among transition metal catalysts, palladium-centered transformations are found to be most versatile, with a wide range of applications on both industrial and laboratory scales [1]. As a result of the growing importance of cross-coupling reactions in organic synthesis over the past few decades, Pd-catalyzed C-X (X=C, N, O, S) bond formation has emerged as an intensively studied area... 

A Concise Account of Recent Sn2 Grignard Coupling Reactions in Organic Synthesis ... 

Pd(0) Coupling Reactions in Organic Synthesis 742 Stereocontrol at Every Step in Asymmetric Allylic Alkylations 745... 

Many reviews have been published in the last few years on the applications of the Hiyama cross-coupling reaction in organic synthesis. In general, preparation of biaryls or heterobiaryls is the most common application of this reaction since new methodology development is based on examples of these. The most prevalent applications of the aryl and heteroaryl halides with organosilane precursors involve reactions such as vinylations, alkenylations, and alkynylations. The reader is encouraged to consult these key reviews. This section will describe some of the more recent applications published in the last few years. 

Kotha, S., Lahiti, K. and Kashinath, D. Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis. Tetrahedron 58, 9633-9695 (2002). Miyaura, N., Yamada, K. and Suzuki, A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett 2ti, 3437-3440 (1979). 

Due to the substantial amount of literature, even when excluding supported catalysts, only selected articles on the solid phase Suzuki reaction are mentioned here, concentrating on the more recent publications. Apart from the general palladium reviews cited in Sect. 5, some examples of solid phase synthesis can be found in a review of apphcations of the Suzuki-Miyaura cross-coupling reactions in organic synthesis by Kotha in 2002 [114]. 

CARRUTHERS Cycloaddition Reactions in Organic Synthesis CLARIDGE High-Resolution NMR Techniques in Organic Chemistry FINET Ligand Coupling Reactions with Heteroatomic Compounds GAWLEY AUBE Principles of Asymmetric Synthesis... 

As shown in recent investigations, catalyzed oxidative coupling of organic molecules provides a new and general route to a variety of hitherto only difficulty accessible polymer systems. While the literature on oxidative coupling reactions in polymer synthesis is already rather extensive, by further investigations of this reaction concept, particularly studies of the catalysis involved, oxidative coupling promises to rival conventional condensation and addition polymerization in importance. 

Carbon-carbon bond formation is one of the most important reaction in organic synthesis [20]. However, most of the reactions require relatively large amounts of a costly transition metal catalyst and its removal from the reaction mixture is difficult. With the perfluoroalkyl substituted triarylphosphane 27 palladium catalyzed cross-coupling reactions of aryl iodides 28 with arylzinc... 

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