Lithium alkylcuprates

Preparation of alkanes using lithium di alkylcuprates (Section 14 11) Two alkyl groups may be coupled together to form an alkane by the reaction of an alkyl hal ide with a lithium dialkylcuprate Both alkyl groups must be primary (or meth yl) Aryl and vinyl halides may be used in place of alkyl halides... 

Reactions of cycloalkadiene monoepoxides have received considerable attention. In general, cyanocu-prates have provided better Sn2 selectivity than lithium homocuprates, and the alternative Sn2 reaction is more competitive with vinyl- or phenyl-cuprates than with alkylcuprate reagents. Reactions of cy-clopentadiene monoepoxides with cyanocuprates have found application in prostaglandin synthesis. Effective electrophilic a -alkylation of cyclic enones can be accomplished by Sn2 cuprate addition to the corresponding epoxy enolate, enol phosphate or silyl enol ether. ... 

Heng and Smith found that the regio-defined enolates resulting from conjugate addition of lithium di-alkylcuprates to enones undergo acceptable aldol additions under the House conditions. One of the... 

The B-alkyl, alkenyl, alkynyl, or aryl-9-BBN derivatives not available via hydroboration are obtained by alkylation of 9-BBN or B-C1-9-BBN or B-MeO-9-BBN with organolithium, Grignard reagent, organocadmium, lithium dialkylcuprates, (phenylthio)alkylcuprates, andhydroboration-carbonylation-reduction. 

Reaction of 1-halogenoallenes or 3-chloroalk-l-ynes with lithium di-alkylcuprates at low temperature is a general route to allenic hydrocarbons (281).222... 

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