Carbon Bonding-Forming Reactions in Organic Synthesis

Chapter 26 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis 

R X is most often a vinyl halide or aryl halide. 

The reaction occurs with syn addition. The position of substituents in the alkene is retained in the cyclopropane. 

Metathesis works best when CH2=CH2, a gas that escapes from the reaction mixture, is formed as one product. 

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Kobayashi S (1999) Lanthanide Triflate-Catalyzed Carbon-Carbon Bond-Forming Reactions in Organic Synthesis. 2 63-118... 

Kobayashi S (1999) Lanthanide triflate-catalyzed carbon-carbon bond-forming reactions in organic synthesis. In Kobayashi S (ed) Topics in organometallic chemistry, vol 2, Lanthanides chemistry and use in organic synthesis. Springer, Heidelberg... 

Michael reactions are one of the most useful carbon-carbon bond-forming reactions in organic synthesis, and Lewis acid-catalysed versions have been developed to solve problems which are often observed in traditional, base-catalysed Michael reactions. Sc(DS)3 can be also applied to Michael reactions in water as shown in Equation (3) [26]. Compared with Yb(OTf)3-catalysed Michael reactions in water [27],... 

Chapter 26 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis covers a few classic reactions that are widely used methods to form complex carbon compounds. This chapter also covers three new methods—Suzuki reaction, Heck reaction, and olefin metathesis. These three methods are now considered mainstays of a synthetic chemist s repertoire of reactions. 

Nair, V., Ros, S., Jayan, C. N., Pillai, B. S. Indium- and gallium-mediated carbon-carbon bond-forming reactions in organic synthesis. Tetrahedron 2004, 60,1959-1982. 

The Michael addition reaction is commonly recognized as one of the most important carbon-carbon bond-forming reactions in organic synthesis, and major efforts have been made to develop efficient catalytic systems for this type of transformation. In particular, the Michael addition of a carbon nucleophile to nitroalkenes is a useful synthetic method for the preparation of nitroalkanes [76], which are versatile synthetic intermediates owing to the various possible easy transformations of the nitro group into other useful functional groups, such as amino groups and nitrile oxides. 

Allylic substitutions are among the most important carbon-carbon bond-forming reactions in organic synthesis. Palladium-catalyzed allylic substitutions and their asymmetric version have been extensively studied and widely used in a variety of total syntheses [78]. The palladium catalysis mostly requires soft nucleophiles such as malonate carbanions to achieve high stereo- and regioselectivity. 

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