Coupling catalyzed

KUMADA NEGISHI Cross coupling Stsreospecific alkenyl aluminum-alkenyl halide cross coupling catalyzed by Pd or Ni... 

The coupling reactions of alkynes and aldehydes catalyzed by iron(III) salts have been discussed above (Scheme 10, routes B and C). The three-component coupling of aldehydes, alkynes, and amines is equivalent to the coupling reaction between alkynes and imines. Wang et al. reported such a three-component coupling catalyzed by FeCls in the absence of any ligand (Scheme 17) [33]. 

Scheme 37 Proposed mechanism of C(sp )-C(sp ) coupling catalyzed by iron(III)...

Table 27.2. Effect of BaCeo95Pdo 0503.5 solvent system on Suzuki coupling" catalyzed by ...

A new oxidation-dehydrogenation-Heck coupling catalyzed by Pd on porous glass or Pd(OAc)2 also proceeded under microwave heating in the MBR (Scheme 2.18) [36]. With an excess of Phi, saturated alcohols including 1-propanol and 3-phenylpro-panol afforded 3,3-diphenylpropenal as the major product, and trans-2,3-diphenylpro-penal by a concerted process taking 10 min at 220 °C. The yields of this remarkable transformation were low, however, and further work into several aspects is required to make them more respectable. 

Following the first observations by Heck that Pd(OAc)2 can substitute a hydrogen atom in ethylene by a carbomethoxy group [50], Stille and James have discovered that the [Pd - Cu] couple catalyzes the incorporation of a COOMe group arising from carbon monoxide and methanol [51]. Most of the reactions with an alkene end up with a diester or a methoxyester, copper being used in stoichiometric quantities. Cyclic alkenes give preferentially diesters (Scheme 7). 

Scheme 8 Miller and co-workers aldehyde imine cross-coupling catalyzed by thiazolylalanine-derived catalysts...

Nucleophilic additions were studied using the same TSIL with pyrrolidine and thiophenol as models. As with the Diels-Alder reaction above, the reaction gave the required adducts which were then transesterified to give the final products. Heck coupling catalyzed by a transition metal and the Stetter reaction, Scheme 30, to prepare 1,4-dicarbonyl compounds were also studied by the same group using similar TSILs. 

Asymmetric Grignard Cross-Coupling Catalyzed by Chiral... 

More recent review Hayashi, T. Asymmetric Grignard Cross-Coupling Catalyzed by Chiral Phosphine-Nickel and Phosphine-Palladium Complexes, in Asymmetric Reactions and Processes in Chemistry (Eliel, E. L., Otsuka, S. ed.), American Chemical Soc. Symp. Series Vol. 185, p. 177 (1982)... 

SCHEME 75. Alkyl-alkyl coupling catalyzed with Ni, Pd or Cu complexes with butadiene dimer... 

STILLE COUPLINGS CATALYZED BY PALLADIUM-ON-CARBON WITH Cul AS A COCATALYST SYNTHESIS OF 2-(4 -ACETYLPHENYL)THIOPHENE1... 

In the next step (R)-reticuline is first transformed to the dienone salutaridine by regioselective para-ortho oxidative coupling, catalyzed by a stereo- and regioselective... 

Among chiral phosphine ligands used for the nickel- or palladium-catalyzed asymmetric cross-coupling, a series of the ferrocenylphosphines has shown a great success in terms of enantioselectivity and a variety of modified chiral ferrocenylphosphines has been applied to the reaction (10-16). The first example of asymmetric cross-coupling catalyzed by... 

Coupling of vinyl iodides with methyl vinyl ketones. Dienones can be obtained in high yield from this coupling, catalyzed by PdCl2(CH3CN)2 prereduced with formic acid. The major dienone formed always possesses the stereochemistry of the vinyl iodide (equation I). 

STILLE COUPLINGS CATALYZED BY PALLADIUM-ON-CARBON WITH 135... 

Scheme 5 Synthesis of tri- and tetra-ortho-substituted biaryl products in KTC coupling catalyzed by Pd-NHC dimer 45...

Table 2 Preparation of chiral binaphthyls in asymmetric Suzuki-Miyaura coupling catalyzed by 79...

Scheme 32 High-order zincates in alkyl-alkyl Negishi coupling catalyzed by 29...

Guyot, S., Vercauteren, J., and Cheynier, V. 1996. Structural determiuatiou of colorless and yellow dimers resulting from (+)-catechin coupling catalyzed by grape polyphenol-oxidase. Phytochemistry 42 1279-88. 

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