Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline
摘要:
AbstractA transition‐metal‐free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10‐phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti‐Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH‐mediated reduction of 1,10‐phenanthroline works as an electron donor and a hydrogen source.
Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide
作者:Eswararao Doni、Shengze Zhou、John Murphy
DOI:10.3390/molecules20021755
日期:——
The coupling of haloarenes to styrenes and 1,1-diarylethenes has been achieved with potassium tert-butoxide in the presence of N,N'-dialkyldiketopiperazines. In contrast to previously reported reactions where phenanthroline has been used to mediate the reactions, the use of diketopiperazines can lead to either 1,1,2-triarylethenes or 1,1,2-triarylethanes, depending on the conditions used.
Catalytic amounts of 1,3-di(methyl)imidazole-2-ylidene, one of the simplest and most prototypical N-heterocyclic carbenes, can up-convert aldehydes into powerful stoichiometric sources of electrons (Super Electron Donors) for reductive transformations of iodoaryls (Ered < −2 V). In particular, the hydroarylation of 1,1′-diarylethylenes, which may require high temperatures and inherently generate stoichiometric
Formation of 2-arylnaphthalenes from N-tosylated phenylalanine derivatives
作者:Mi Ra Seong、Hyun Nam Song、Jae Nyoung Kim
DOI:10.1016/s0040-4039(98)01507-x
日期:1998.9
N-Tosylated phenylalanine derivatives in benzene in the presence of sulfuric acid afforded 2-arylnaphthalene derivatives in moderate yields. The reaction might proceed via the corresponding decarbonylated N-tosylimine derivatives. Aldol type reaction of N-tosylimines followed by intramolecular Friedel-Crafts reaction and elimination of p-toluenesulfonamide gave 2-arylnaphthalenes. (C) 1998 Elsevier Science Ltd. All rights reserved.