116195-81-4Relevant articles and documents
Preparation and Properties of Pyridine-Analogue of TCNQ Dianion Salt
Hama, Yoshiyuki,Nobuhara, Yukikazu,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1683 - 1687 (1988)
Bis(tetrapropyl- and tetrabutylammonium) 1,1'-(2,5-pyridinediyl)bis (4a and 4b) were prepared in order to investigate the properties of pyridine-analogue 3 of TCNQ as a new electron acceptor and its complexation with TTF.Although 3 was not isolated, the cyclic voltammetry of the salt 4 indicated that 3 was a stronger electron acceptor than TCNQ.The charge-transfer complex of TTF and 3 was prepared by mixing TTF with 3 which was generated in situ from electrolytic oxidation of 4 or from the oxidation of 2,5-bis(dicyanomethyl)pyridine, a precursor of 4, with hydrogen peroxide.It consisted of 1:1 composition of donor and acceptor and showed a high electrical conductivity of 19 Scm-1.The 2:1 complex was prepared by metathesis of (TTF)3(BF4)2 and 4, and also highly conductive.
Cheap and easy synthesis of highly functionalized (het)aryl iodides via the aromatic finkelstein reaction
Meyer-Eppler, Georg,Kuechler, Lea,Tenten, Christina,Benkhaeuser, Christian,Brueck, Stefanie,Luetzen, Arne
, p. 1085 - 1090 (2014/05/06)
Aryl iodides are superior coupling partners in cross-couplingA- reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2′-bipyridines, and chiral compounds. Georg Thieme Verlag Stuttgart? New York.
Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines
Chau, Nguyet Trang Thanh,Meyer, Maxime,Komagawa, Shinsuke,Chevallier, Floris,Fort, Yves,Uchiyama, Masanobu,Mongin, Florence,Gros, Philippe C.
experimental part, p. 12425 - 12433 (2011/01/05)
Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.