84648-44-2Relevant academic research and scientific papers
Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
Laulhé, Sébastien,Blackburn, J. Miles,Roizen, Jennifer L.
supporting information, p. 4440 - 4443 (2016/09/09)
Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.
Effects of substituents on NMR chemical shifts and mass fragmentation patterns of 1-aryl-3-phenylpropanes
Jeong, Eun Jeong,Lee, In-Sook Han
, p. 538 - 543 (2016/04/26)
The 1H and 13C chemical shifts and the mass spectral fragmentation patterns of 1-aryl-3-phenylpropanes with m- or p-substituents (H, NO2, Br, Cl, OCH3, CH3) were studied. The electronic effects of the substi-tuents seemed to be transmitted by the through-space as well as by a through-bond mechanism, resulting in an inverse correlation in the plot of the chemical shift values of i-C vs. the Hammett σ values. The mass spectra showed the substituted benzyl fragments as the base peaks when the substituents were electron donating, whereas the benzyl fragment was observed as the base peaks with the electron-withdrawing substituents.
Copper-Catalyzed Boron-Selective C(sp2)-C(sp3) Oxidative Cross-Coupling of Arylboronic Acids and Alkyltrifluoroborates Involving a Single-Electron Transmetalation Process
Ding, Siyi,Xu, Liang,Li, Pengfei
, p. 1329 - 1333 (2016/02/18)
A rapid and highly selective oxidative cross-coupling reaction between readily available and shelf-stable arylboronic acids and primary or secondary potassium alkyltrifluoroborates was devised and developed, which works under mild conditions using copper(II) acetate as the catalyst and silver oxide as the oxidant. Initial experimental results indicate that a single-electron transmetalation process is involved. This approach effectively bypasses the problems associated with the traditional cross-coupling reactions of alkylboronates and thus provides a complementary method in building C(sp2)-C(sp3) bonds.
Structure of ω-Arylalkyl Radicals: A 13C CIDNP Investigation
Olah, George A.,Krishnamurthy, V. V.,Singh, Brij P.,Iyer, Pradeep S.
, p. 955 - 963 (2007/10/02)
Thermolysis of a series of ω-arylalkanoyl m-chlorobenzoyl (and acetyl) peroxides at ca. 100 deg C in cyclohexanone and in hexachloroacetone was studied by using 13C chemically induced dynamic nuclear polarization.Analysis of the observed 13C polarizations indicate that all the three radicals (β-arylethyl, γ-arylpropyl and δ-arylbutyl) have open-chain structures with no evidence for aryl participation resulting in spirocycloalkylcyclohexadienyl radicals.
