24006-92-6Relevant articles and documents
2,3-Dihalo- and 2,3,6,7-Tetrahaloanthracenes by Vollhardt Trimerization
Hoffmann, Hendrik,Mukanov, Diana,Ganschow, Michael,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.
, p. 9826 - 9834 (2019/08/20)
We efficiently synthesized otherwise difficult to obtain 2,3- and 2,3,6,7-halogenated anthracenes with diverse east/west substituents. Key steps involve the (i) Vollhardt cyclization of bis(propargyl)benzenes with bis(trimethylsilyl)acetylene, (ii) halo-desilylation introducing chlorine, bromine, or iodine substituents, and (iii) dehydrogenation. Pd catalysis allows selective functionalization at the anthracenes' east/west positions. A tetrahydropentacene is synthesized and derivatized via the same strategy, employing tetrapropargylbenzene.
Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials
Yamamoto, Koji,Takagi, Akuto,Hada, Miyako,Taniwaki, Ryosuke,Mizutani, Tadashi,Kimura, Yoshifumi,Takao, Yuko,Moriwaki, Kazuyuki,Matsumoto, Fukashi,Ito, Takatoshi,Iwai, Toshiyuki,Hida, Koichi,Mizuno, Takumi,Ohno, Toshinobu
, p. 4918 - 4924 (2016/07/18)
Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower H
Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence
Pea-Lpez, Miguel,Neumann, Helfried,Beller, Matthias
, p. 865 - 871 (2015/03/14)
The synthesis of lactones and lactams by using iron(II) pincer-catalyzed dehydrogenative methodology was developed. Starting from 1,n-diols or 1,n-amino alcohols, this domino transformation takes place through initial dehydrogenation of the substrates, subsequent intramolecular cyclization, and final oxidation to afford the desired products in good yields. The ability to access heterocycles of different sizes makes this protocol especially versatile, in which two consecutive oxidation reactions are performed without requiring an external oxidant. In this paper, we report the application of the Fe-MACHO-BH complex [carbonylhydrido(tetrahydroborato)[bis(2-diisopropylphosphinoethyl)amino]iron(II)] in this atom-efficient and environmentally benign process, for which molecular hydrogen is formed as the only stoichiometric side product. Just a little pinch: The iron(II) pincer-catalyzed synthesis of lactones and lactams from easily available 1,n-diols and 1,n-amino alcohols is explored. The use of a nontoxic metal as well as the generation of molecular hydrogen as the only stoichiometric byproduct makes this method a highly atom-efficient and environmentally benign process.