- Aryl Radical Selectivity in Biphasic Systems
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Aryl radicals generated in the aqueous phase of biphasic mixtures have-regardless of a comparably low polarity- A strong preference to react with aromatic substrates in the aqueous phase and not to undergo phase-transfer into a lipophilic phase, independent from the presence of a surfactant. These results represent an important prerequisite toward future studies in biological systems, which typically consist of various compartments of either hydrophilic or lipophilic character.
- Altmann, Lisa-Marie,Fürst, Michael C. D.,Gans, Eva I.,Heinrich, Markus R.,Pratsch, Gerald,Zantop, Viviane
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supporting information
(2020/01/31)
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- Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes
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Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temp
- Thon, Daniel,Fürst, Michael C.D.,Altmann, Lisa-Marie,Heinrich, Markus R.
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p. 5289 - 5294
(2018/07/06)
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- Visible-Light-Induced, Catalyst-Free Radical Arylations of Arenes and Heteroarenes with Aryldiazonium Salts
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In the absence of a photocatalyst and other additives, the radical arylation of diverse arenes and heteroarenes has been achieved with aryldiazonium salts under visible-light irradiation from a blue light-emitting diode (LED). Although the course of some reactions can be rationalized by the formation of strongly light-absorbing charge-transfer (CT) complexes between the diazonium ion and the aromatic substrate, several further examples indicated that the simple presence of an aromatic substrate, showing only weak interactions to the diazonium ion, is fully sufficient to enable product formation.
- Fürst, Michael C. D.,Gans, Eva,B?ck, Michael J.,Heinrich, Markus R.
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supporting information
p. 15312 - 15315
(2017/10/20)
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- Synthesis of 6-Arylpyridin-3-ols by Oxidative Rearrangement of (5-Arylfurfuryl)amines
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The synthesis of 6-arylpyridin-3-ols and their 2,4-dibrominated analogues has been achieved by the oxidative rearrangement of (5-arylfurfuryl)amines. The desired arylpyridols were obtained in good to high yields, and the reactions were shown to be suitable for preparation on a gram scale.
- Fürst, Michael C. D.,Sauer, Caroline S.,Moriyama, Takaaki,Kamimura, Akio,Heinrich, Markus R.
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supporting information
p. 3051 - 3055
(2016/07/12)
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- Radical arylation of phenols, phenyl ethers, and furans
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Radical arylations of parasubstituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titaniumACHTUNGTRENUNG(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access todiversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxyl groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a b-secretase inhibitor and the synthesis of a calciumchannel modulator
- Wetzel, Alexander,Pratsch, Gerald,Kolb, Roman,Heinrich, Markus R.
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experimental part
p. 2547 - 2556
(2010/06/17)
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