Hidenori Someya

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Silver salts catalyze the benzylation and allylation of tertiary alkyl bromides with organozinc reagents. The reactions create quaternary carbon centers efficiently. Treatment of gem-dibromoalkanes with benzylic or allylic zinc reagents under silver catalysis leads to dibenzylation or diallylation. The functional-group compatibility of the present reactions(More)
[reaction: see text] N-Heterocyclic carbene/cobalt systems effectively catalyze sequential cyclization/cross-coupling reactions of 6-halo-1-hexene derivatives with trialkylsilylmethyl and 1-alkynyl Grignard reagents, which phosphine and amine ligands did not promote.
Treatment of alkyl halides, including tertiary alkyl bromides, with cyclopentadienylmagnesium bromide in the presence of a catalytic amount of copper(II) triflate yielded the corresponding cyclopentadienylated products in high yields. The following hydrogenation of the products provided alkyl-substituted cyclopentanes.
[chemical reaction: see text]. Diorganophosphide anions, which usually function as nontransferable ligands on mixed cuprates, undergo smooth 1,2-migration on ate-type copper carbenoids. Phosphinodisilylmethylcoppers prepared by this protocol are converted into the corresponding phosphines, which can be used as bulky, highly basic and air-stable ligands.
Treatment of alkyl halides, including tertiary alkyl bromides, with benzylic or allylic Grignard reagent in the presence of a catalytic amount of silver nitrate in ether yielded the corresponding cross-coupling products in high yields. The coupling reactions of tertiary alkyl halides provide efficient access to quaternary carbon centers.
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