A versatile organozinc approach to the synthesis of potential organic functional building blocks: 5-substituted 3-bromo-2-methylthiophene derivatives
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Cheon, Jong-Woo,Cho, Hyun-Hee,Kim, Seung-Hoi
p. 1266 - 1269
(2015/07/15)
Site-selective mono-oxidative addition of active zinc into carbon-bromine bond of dibrominated-thiophenes: Preparation of thienylzinc reagents and their applications
A facile protocol for the preparation of 3-bromo-2-thienylzinc bromide A and 5-bromo-2-thienylzinc bromide B has been developed. It has been successfully accomplished by a site-selective oxidative addition of active zinc into a chemically pseudo-equivalent or equivalent carbon-bromine bond, respectively. The subsequent cross-coupling reactions of the organozincs were also successfully carried out under mild conditions providing the corresponding products in moderate to high yields.
Jung, Hye-Soo,Cho, Hyun-Hee,Kim, Seung-Hoi
p. 960 - 964
(2013/02/25)
New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust
A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.
Fillon, Hyacinthe,Gosmini, Corinne,Perichon, Jacques
p. 3867 - 3870
(2007/10/03)
New and efficient access to 3-substituted 2,5-dibromothiophenes. Consecutive nickel-catalyzed electrochemical conversion to thienylzinc species
We have achieved the stepwise synthesis of 3-substituted thienylzinc reagents using both electrochemical methods and an original bromination procedure. For several compounds 3-bromothiophene was the starting substrate, which was functionalized according to recently developed electrochemical procedures. The nickel-catalyzed electrochemical reduction of the resulting 3-substituted 2,5-dibromothiophenes in the presence of zinc salts allowed the formation of monothienylzinc species in good yields. The selectivity of this reaction is discussed within the context of the electrochemical synthesis of regioregular polythiophenes.
Mellah,Labbe,Nedelec,Perichon
p. 318 - 321
(2007/10/03)
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