31161-44-1Relevant academic research and scientific papers
Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
Zhao, Hang,Dankwardt, John W.,Koenig, Stefan G.,Singh, Surendra P.
supporting information; experimental part, p. 166 - 169 (2012/01/30)
A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.
Dehalogenation of 1-Halogenothienyl-di- and -tetra-hydroisoquinolines by Sodium Methoxide in Dimethyl Sulphoxide
Barker, John M.,Huddleston, Patrick R.,Clephane, Janette,Wood, Michael L.,Holmes, David
, p. 275 - 282 (2007/10/02)
On treatment with sodium methoxide-dimethyl sulphoxide (NaOMe-DMSO) 1-(5-halogeno-2-thienyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolines suffer loss of halogen and are converted into the related 1-hydroxytetrahydroisoquinolines.The reaction fails with comparable 1-bromophenyl- and 1-(halogeno-3-thienyl)tetrahydroisoquinolines.A similar transformation takes place with (5-halogeno-2-thienyl)phenylmethoxymethanes, leading to the dimethyl acetal of the 5-dehalogenated-2-thienyl phenyl ketone. α-Halogenated-2 and 3-thienyl-3,4-dihydroisoquinolines undergo dehalogenation-aromatisation with NaOMe-DMSO.Mechanisms for these conversions are proposed.
CATALYTIC REDUCTIVE DEBROMINATION - A NEW METHOD FOR THE PREPARATION OF DEUTERO-SUBSTITUTED THIOPHENES AND FURANS
Sharf, V. Z.,Belen'kii, L. I.,Gurovets, A. S.,Karmanova, I. B.
, p. 134 - 138 (2007/10/02)
The principles of the reductive dehalogenation of a number of mono- and dibromo-substituted functional derivatives of thiophene and furan in the presence of a palladium complex applied to silica gel modified with γ-aminopropyl groups were investigated.A one-step method for the preparation of mono- and dideutero-substituted carbonyl compounds of the furan and thiophene series was developed.
