C—P cross-coupling

Stadler, A. and Kappe, C.O., Rapid formation of triarylphosphines by microwave-assisted transition metal-catalysed C-P cross-coupling reactions, Org. Lett., 2002, 4, 3541-3543. 

Table 8 Pd-catalyzed C-P cross-coupling according to Equation (21)...

Transition metal-catalyzed C—P cross-coupling affords powaful tool for the preparation of aryl phosphorus compounds [198]. The scope of the phosphorus-based nucleophiles used in crosscoupling with aryl electrophiles in the presence of transition metal (Pd-, Cu-, and Ni-based) catalysts is very broad. Figure 20.5 summarizes the common phosphoms nucleophiles used for crosscoupling reactions (for mechanism, see Scheme 20.2). 

Imamoto and coworkers described phosphine-borane complexes as a coupling partner for the synthesis of aryl phosphines with aryl electrophiles using Pd(PPh3),j at room temperature (Scheme 20.68) [228,229], The borane moiety can be easily removed ljy excess use of diethyl amine or morpholine. Gaumont and coworkers demonstrated the palladium-catalyzed C—P cross-coupling in imidazolium-based ionic liquid and that the catalyst can be recycled up to six cycles [230]. 

SCHEME 4321 Copper oxide-catalyzed decarboxylative C—P cross-coupling [482]. 

Tappe FMJ, Trepohl VT, Oestreich M. Transition-metal-catalyzed C—P cross-coupling reactions. Synthesis 2010 18 3037-3062. 

Combs, A.P., Saubern, S., Rafalski, M. and Lam, P.Y.S., Solid supported aryl/heteroaryl C—N cross-coupling reactions, Tetrahedron Lett., 1999, 40, 1623-1626. 

Similarly, the change in resinols C from being almost entirely derived from sinapyl alcohol in the wild-type to being derived from all three monomers, and p-coumaryl alcohol in particular, in the transgenic plants, is striking. It is logical that sinapyl alcohol monomers find themselves only rarely able to dimerize (with other sinapyl alcohol monomers) in this sinapyl-alcohol-depleted plant, so presumably P-P-cross-couple with coniferyl, and possibly p-coumaryl alcohol studies are... 

The C—O cross-coupling of primary and secondary alcohols with aryl halides has been synthetically challenging due to p-hydride elimination (Schane 20.38, see Scheme 20.2). This has been overcome using binaphthyl-based phosphines L98 and L90 [112]. Buchwald and coworkers have explored sterically hindered phosphines for the alkoxylation of aryl substrates with secondary alcohols, and ligands L99-L100 with 1-phenyl and naphthyl backbone exhibited superior results (Scheme 20.39) [113]. 

Ranjit S, Duan Z, Zhang P, Liu, X. Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C—S cross-coupling. Org. Lett. 2010 12 4134- 136. 

Duan Z, Ranjit S, Zhang P, Liu X. Synthesis of aryl sulfides by decarboxylic C—S cross-couplings. Chem. Eur. J. 2009 15 3666-3669. 

Ramana T, Sha P, Das M, Punniyamurthy T. Copper-catalyzed domino intra and intermolecular C—S cross-coupling reactions synthesis of 2-(arylthio)arylcyanamides. Org. Lett. 2010 12 84-87. 

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). 

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