Halides alkyl, coupling with

A variety of organometallic compoundshave been used to couple with alkyl halides. " Organosodium and organopotassium compounds are more reactive than Grignard reagents and couple even with less reactive halides. Organolithium... 

Grignard reagents can be made to couple with alkyl halides in good yields by the... 

Haloalkynes (R—C=C—X) react with ArSnBu3 and Cul to give R—C= C—Ar. Acetylene reacts with two equivalents of iodobenzene, in the presence of a palladium catalyst and Cul, to give 1,2-diphenylethyne. 1-Trialkylsilyl alkynes react with 1-haloalkynes, in the presence of a CuCl catalyst, to give diynes and with aryl triflates to give 1-aryl alkynes. Alkynes couple with alkyl halides in the presence of Sml2/Sm. Alkynes react with hypervalent iodine compounds " and with reactive alkanes such as adamantane in the presence of AIBN. ... 

Even alkyl Grignard reagents can be coupled with alkyl halides 1 using iron catalysis with the xantphos ligand 11 (entry 16) [56]. The yields are acceptable for primary alkyl bromides. Secondary alkyl halides reacted only in low yield. 

The more reactive ft -carbon atom of ketone a,/ -dianions can be regiospecifically coupled with alkyl halides to give first lithium enolates, which are then trapped by more reactive carbon electrophiles such as allylic halides. The first example shown in Table 8 deals with the sequential /1-alkylation and ce-allylation of a ketone a,/1-dianion1 13. Thus, the dianion underwent regioselective alkylation at the ft carbon with //-pentyl bromide and then allylation with allyl bromide at the a carbon. When an excess of allyl bromide is reacted with the a, ft -dianion, the diallylated product is obtained in a good yield, whereas a threefold excess of pentyl bromide only resulted in the formation of the ft-alkylation product. Similar consecutive alkyl/allyl-type reactions are also possible for ketone a,5-dianions14. 

Lithium diorganocopper reagent (Gilman reagent), LiR2Cu Couples with alkyl halides to yield alkanes (Section 10.8). 

Alkynes couple with alkyl halides in the presence of Sml2/Sm. Alkynes react... 

Alkylboronic acids are coupled to aryl halides using a palladium catalyst, " analogous to the Suzuki reaction in 13-12. Conversely, arylboronic acids can be coupled to aliphatic halides Arylboronic acids can be coupled to allylic alcohols as well. " Arylboronic acids (12-28) were shown to react directly with benzene in the presence of Mn(OAc)3. " Arylboronic acids also couple with alkyl halides in... 

In nonaqueous solution azomethine compounds are usually stable, and several types have been reductively coupled with alkyl halides or carbon dioxide. Benzophenone anil (III) gives thus on reduction in DMF-TBAI in the presence of methyl chloride a mixture of N- and C-methylated and N,C-dimethylated products [28] ... 

Triphenylthiopyrylium salts and some other trisubstituted thiopyrylium compounds show two reversible redox systems [185] the anion from the second reduction has been used as electron transfer agent in indirect reduction of and coupling with alkyl halides [199]. 

The nucleophilic SnfNfSiMejf ] reacts with various aUylic halides, and the resulting allyltin(IV) species are a source of allyl radicals. Thus, in the presence of AIBN, coupling with alkyl halides occurs. 

This reaction has been modified to undergo the coupling with alkyl halides using the combination of PdBr2/P( -Bu)2Me/TBAF as a catalytic system. ... 

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