16494-36-3Relevant articles and documents
Highly tin-selective stille coupling: Synthesis of a polymer containing a stannole in the main chain
Linshoeft, Julian,Baum, Evan J.,Hussain, Andreas,Gates, Paul J.,N?ther, Christian,Staubitz, Anne
, p. 12916 - 12920 (2014)
The incorporation of heavier Group 14 element heteroles into semiconducting polymers leads to unusual optoelectronic properties. However, polymers containing stannoles have not been accessible to date. We report a synthetic route to a well-defined, stannole-containing polymer, the first example of this class of π-conjugated polymers. This route was made possible by developing difunctionalized stannole monomers and highly tin-selective Stille coupling reactions that leave the tin in the stannole untouched. Compared to poly(3-n-hexylthiophene), the resulting polymer displays a remarkable bathochromic shift in its absorption. The budding potential of stannoles: A stannole monomer is prepared and employed in a highly tin-selective Stille coupling, giving a well-defined and non-annulated stannole-containing polymer, the first example from this class of π-conjugated polymers. Compared to polythiophenes, a strong bathochromic shift in the absorption spectrum was observed.
Synthesis of thiophene/phenylene co-oligomers. III [1]. Thienyl-capped oligophenylenes
Hotta
, p. 923 - 927 (2001)
The author reports the synthesis of thienyl-capped oligophenylenes via improved synthetic schemes. These schemes are based on either the Grignard or Suzuki coupling reaction and enable the author to obtain the target compounds at appreciably high yields. Regarding several of these compounds, their synthesis and characterization are believed to be reported for the first time. The resulting materials have been fully characterized through the nmr and ir spectroscopy. The ir analysis is particularly useful in characterizing the materials of higher molecular weight, since those materials are difficult to dissolve in organic solvents.
Photo-oxidative Cross-Dehydrogenative Coupling-Type Reaction of Thiophenes with α-Position of Carbonyls Using a Catalytic Amount of Molecular Iodine
Sudo, Yusuke,Yamaguchi, Eiji,Itoh, Akichika
supporting information, p. 1610 - 1613 (2017/04/13)
A metal-free photo-oxidative intermolecular C-H/C-H coupling reaction of thiophenes is demonstrated with carbonyls using a catalytic amount of molecular iodine. In this system, molecular oxygen in the air acted as a terminal oxidant to regenerate molecular iodine. A mechanistic study was also performed.
Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
, p. 74 - 96 (2013/04/10)
The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
