Cross-coupling reactions with alkyl halides

3 Cross-coupling Reactions with Alkyl Halides 

---

Fig. 2 Catalysts and ligands used in iron-catalyzed cross-coupling reactions with alkyl halides...

B. Cross-coupling Reactions with Alkyl Halides. 1277... 

Iron-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Organometallic Reagents... 

Fig. 3 Catalytic manifolds in iron-catalyzed cross-coupling reactions of alkyl halides 1 with organometallic species 2...

Tamura and Kochi studied the cross-coupling reactions of alkyl halides with alkyl Grignard reagents catalyzed by silver compounds first [422, 426, 427]. The coupling of primary alkyl halides with primary Grignard reagents resulted in a mixture... 

Alkyl(trifluoro)silanes are also applicable to the cross-coupling reaction with aryl halides (Eq. 34) [41,42]. TBAF in excess is required for giving products in acceptable yields, as the coproduced Sip4 is readily converted into (SiFs) or (SiFa)2-. 

Cross-coupling reaction of alkyl halides with grignard reagents in the presence... 

CROSS-COUPLING REACTION OF ALKYL HALIDES WITH GRIGNARD REAGENTS IN THE PRESENCE OF 1,3-BUTADIENE CATALYSED BY NICKEL, PALLADIUM, OR COPPER... 

Cross-Coupling Reaction of Alkyl Halides with Grignard Reagents Catalyzed by Ni, Pd, or Cu Complexes with n-Carbon Ligand(s) Terao, J. Kambe, N. Acc. Chem. Res. 2008,... 

Historically, the first report of the Pd-catalyzed cross-coupling reaction with acyl halide used organomercury compounds. Although alkyl- and arylmercury chlorides did not work, the use of dialkyl- and diarylmercury compounds gave the desired ketones in good yields. Acyl bromides are necessary to bring about fruitful results. The use of HMPA as the solvent is also unavoidable (Scheme 9). 

In addition to the cross-coupling reactions of alkyl halides or sulfonates with organometallic nucleophiles, the former can also directly undergo C-C bond formation with nonactivated C-H bonds of alkenes or arenes in a Heck-type reaction. Iron-catalyzed intramolecular dehydrohalogenation of 2-iodoethanal alkenyl acetals with phenyl-magnesium bromide in the presence of a catalytic amount of iron(II) chloride provides tetrahydrofliran derivatives in moderate yields (Scheme 4-240). Allyl 2-halophenyl ethers provide dihydrobenzofiiran derivatives under these conditions. ... 

Organozinc compounds have been extremely useful reagents in the Negishi cross-coupling reactions with alkyl and aryl halides creating a new C—C bond (Scheme 13.28). The Negishi Ni, Pd, or Fe mediated cross-coupling reactions have proved to be powerful tools in vast areas of synthesis. 

Scheme 4.82 Cross-coupling reactions of alkyl halides with arylmagnesium derivatives.

---