- Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues
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A series of alkylated 2,3-dihydroxybiphenyls has been prepared on the gram scale by using an effective Directed ortho Metalation–Suzuki–Miyaura cross-coupling strategy. These compounds have been used to investigate the substrate specificity of the meta-cl
- Nerdinger, Sven,Kuatsjah, Eugene,Hurst, Timothy E.,Schlapp-Hackl, Inge,Kahlenberg, Volker,Wurst, Klaus,Eltis, Lindsay D.,Snieckus, Victor
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- Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates
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A general method for synthesis of 1,2-bis-trifluoromethylthioarenes has been developed. Arynes generated from silyl aryl triflates or halides react with bis(trifluoromethyl)disulfide to afford 1,2-bis-trifluoromethylthioarenes. Aryl, alkyl, ester, halide,
- Mesgar, Milad,Daugulis, Olafs
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supporting information
p. 4247 - 4250
(2017/08/23)
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- Double N-arylation of primary amines: Carbazole synthesis from 2,2′-biphenyldiols
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(Chemical Equation Presented) The double N-arylation of primary amines with 2,2′-biphenylylene ditriflates was investigated for the synthesis of multisubstituted carbazoles. Palladium complexes supported by 2-dicyclohexylphosphino-2′-methylbiphenyl or Xantphos [4,5- bis(diphenylphosphino)-9,9-dimethylxanthene] were found to be efficient catalysts for the reaction. The catalysts allow the use of anilines with an electron-donating or electron-withdrawing substituent and multisubstituted 2,2′-biphenylylene ditriflates as substrates. Ammonia equivalents, such as O-tert-butyl carbamate, are also employable as a nitrogen source to give the N-protected carbazoles which can easily give the corresponding N-unsubstituted carbazoles after deprotection. By using this methodology, a carbazole alkaloid, mukonine, is synthesized in 40% yield for five steps, in comparable efficiency to the recent precedents.
- Kuwahara, Atsushi,Nakano, Koji,Nozaki, Kyoko
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p. 413 - 419
(2007/10/03)
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- The biosynthesis of ubiquinone: Synthesis and enzymatic modification of biosynthetic precursors
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The synthesis of key intermediates in the eukaryotic biosynthetic pathway of ubiquinone (Q) and the biotransformation of these materials with yeast (S.cerevisiae) mitochondria are described. The synthesis of Q aromatic precursors 2, 3, and 4 (n = 3 in all cases) relies on the palladium (0) catalyzed coupling of farnesyl tributylstannane with suitably functionalized aryl halides. Preliminary experiments show that incubation of synthetic substrate 3 with mitochondria from yeast containing the 3,4-dihydroxy-5-hexaprenylbenzoate methyltransferase gene (COQ3) and S-[methyl-3H]adenosyl-L-methionine yields radiolabeled 4.
- Shepherd, Jennifer A.,Poon, Wayne W.,Myles, David C.,Clarke, Catherine F.
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p. 2395 - 2398
(2007/10/03)
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