42079-83-4Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles
Pena-Lopez, Miguel,Ayan-Varela, Miguel,Sarandeses, Luis A.,Perez Sestelo, Jose
supporting information; experimental part, p. 9905 - 9909 (2010/10/19)
The palladium-catalyzed cross-coupling reaction of organogold(I) reagents (alkyl, alkenyl, aryl, and alkynyl) with organic electrophiles, such as aryl and alkenyl halides, aryl triflates, benzyl bromide, and benzoyl chloride is reported. The reaction takes place, under palladium catalysis, at room temperature with short reaction times to give the corresponding cross-coupling products in high yields.
Cobalt- and rhodium-catalyzed cross-coupling reaction of allylic ethers and halides with organometallic reagents
Yasui, Hiroto,Mizutani, Keiya,Yorimitsu, Hideki,Oshima, Koichiro
, p. 1410 - 1415 (2007/10/03)
Reactions of 2-alkenyl methyl ether with phenyl, trimethylsilylmethyl, and allyl Grignard reagents in the presence of cobalt(II) complexes are discussed. The success of the reactions heavily depends on the combination of the substrate, ligand, and Grignard reagent. In the reaction of cinnamyl methyl ether, the formation of the linear coupling products predominates over that of the relevant branched products. In the cobalt-catalyzed allylation of allylic ethers, addition of a diphosphine ligand can change the regioselectivity, mainly providing the corresponding branched products. Rhodium complexes catalyze the reactions of allylic ethers and halides with allylmagnesium chloride and allylzinc bromide, respectively, in which the branched coupling product is the major product.
Cobalt-catalyzed allylic substitution reaction of allylic ethers with phenyl and trimethylsilylmethyl grignard reagents
Mizutani, Keiya,Yorimitsu, Hideki,Oshima, Koichiro
, p. 832 - 833 (2007/10/03)
Treatment of cinnamyl methyl ether with phenylmagnesium bromide in ether in the presence of CoCl2[1,5-bis(diphenylphosphino)pentane] affords 1,3-diphenylpropene in good yield. Similar allylic substitution reaction with trimethylsilylmethylmagne
Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents
Mechelke, Mark F.,Wiemer, David F.
, p. 4821 - 4829 (2007/10/03)
The synthesis of a family of farnesol analogues, incorporating aromatic rings, has been achieved in high yields through the development of a regioselective coupling of allylic tetrahydropyranyl ethers with organometallic reagents. The allylic THP group is displaced readily by Grignard reagents in the presence of Cu(I) halides but is stable in the absence of added copper. Thus, an allylic THP group can fulfill its traditional role as a protecting group or serve as a leaving group depending on reaction conditions. An improved synthesis of (2E,6E)-10,11-dihydrofarnesol also has been accomplished using this methodology, and some preliminary studies on the reactivity and regioselectivity of THP ether displacements were conducted. The farnesol analogues reported herein may be useful probes of the importance of nonbonding interactions in enzymatic recognition of the farnesyl chain and allow development of more potent competitive inhibitors of enzymes such as farnesyl protein transferase.
Regioselectivity in the nickel-catalysed coupling of cyclic carbonytes of but-3-ene-1,2-diols with organoborates
Mizojiri, Ryo,Kobayashi, Yuichi
, p. 2073 - 2076 (2007/10/02)
The regioselectivity of nickel-catalysed coupling of but-3-ene-1,2-diol cyclic carbonates 1 and organoborates 3 is examined, in which an ester or olefin directs the coupling site to afford conjugated products.
Synthesis of 1-Arylalk-2-enes and 1-Arylalkanes via Friedel-Crafts Alkylation with Allylic Alcohols Catalysed by an Acidic Clay
Smith, Keith,Pollaud, Guy M
, p. 3519 - 3520 (2007/10/02)
Moderately activated benzenoid compounds undergo alkylation with allylic alcohols in the presence of acidic K10 clay to give almost exclusively 1-arylalk-2-enes by attack at the terminal position of the intermediate allyl cation; catalytic hydrogenation yields the corresponding 1-arylalkanes.
Arylation of Olefins by N-Nitroso-N-arylacetamides under Palladium(0) Catalysis: A New Precursor of Arylpalladium Species
Kikukawa, Kiyoshi,Naritomi, Masaki,He, Gong-Xin,Wada, Fumio,Matsuda, Tsutomu
, p. 299 - 301 (2007/10/02)
Olefins (styrene, octene-1, cycloheptene, ethyl acrylate, and vinyl acetate) were easily arylated in good yields with N-nitroso-N-arylacetamides (ArN(NO)COCH3: Ar= Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, and 4-IC6H4) under palladium(0) catalysis at 40 deg C within 40 min.
Palladium(0)-Catalyzed Arylation of Olefins by Arylamines and an Alkyl Nitrite
Kikukawa, Kiyoshi,Maemura, Koji,Kiseki, Yasuyuki,Wada, Fumio,Matsuda, Tsutomu,Giam, Choo S.
, p. 4885 - 4888 (2007/10/02)
Various olefins were arylated by the combination of arylamines and tert-butyl nitrite under palladium catalysis in the presence of acid such as monochloroacetic or acetic.The reaction proceeded in good yields without serious effects from substituents on either the olefinic substrates or the arylamines, including 3-aminopyridine.
