63361-60-4Relevant academic research and scientific papers
Unusual Regiospecificity in Syn Elimination from trans-2-Chloro-3-fluoro-2,3-dihydrobenzofuran Promoted by Complex Base
Bartsch, Richard A.,Cho, Bong Rae,Pugia, Michael J.
, p. 5494 (1987)
Elimination from trans-2-chloro-3-fluoro-2,3-dihydrobenzofuran induced by NaNH2-NaO-t-Bu in THF results in syn dehydrofluorination to the exclusion of β-aryl-activated syn dehydrochlorination.
Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)
Ji, Yong,Li, Pinhua,Zhang, Xiuli,Wang, Lei
supporting information, p. 4095 - 4101 (2013/07/05)
An intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to give 2-bromobenzofurans(thiophenes) in the presence of a trace amount of Cu (0.0064 mol%, 25 ppm) has been developed. The reaction provides the desired products in excellent yields under fluoride-free and mild reaction conditions and with a TON (turnover number) of up to 1.5 × 104. The Royal Society of Chemistry 2013.
Metal-free chlorodeboronation of organotrifluoroborates
Molander, Gary A.,Cavalcanti, Livia N.
experimental part, p. 7195 - 7203 (2011/10/13)
A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.
A highly efficient TBAF-promoted intramolecular cyclization of gem-dibromoolefins for the synthesis of 2-bromobenzofurans(thiophenes)
Chen, Wei,Zhang, Yicheng,Zhang, Lei,Wang, Min,Wang, Lei
supporting information; experimental part, p. 10476 - 10478 (2011/10/31)
A highly efficient tetra-(n-butyl)ammonium fluoride (TBAF)-promoted intramolecular cyclization of gem-dibromoolefins has been developed for the synthesis of 2-bromobenzofused heterocycles. The reaction provides a convenient approach to 2-bromobenzofurans(
Modulating reactivity and diverting selectivity in palladium-catalyzed heteroaromatic direct arylation through the use of a chloride activating/blocking group
Liegault, Benoit,Petrov, Ivan,Gorelsky, Serge I.,Fagnou, Keith
supporting information; experimental part, p. 1047 - 1060 (2010/04/04)
(Chemical Equation Presented) Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.
Benzofuran derivatives useful as inhibitors of mammalian leukotriene biosynthesis
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, (2008/06/13)
Benzofuran derivatives, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic condit
SYNTHESIS OF 2,3-DIHALOGENO-2,3-DIHYDROBENZOFURANS: REGIOSELECTIVITY AND STEREOCHEMISTRY
Perugini, Renzo,Ruzziconi, Renzo,Sebastiani, Giovanni V.
, p. 149 - 152 (2007/10/02)
The synthesis of a series of bromochloro- and chlorofluoro-2,3-dihydrobenzofurans has been carried out.In the bromochlorination of benzofuran trans adducts were obtained and a dependence of the reaction regioselectivity on the solvent polarity and the halogenating species was observed.The reaction of silver fluoride with the trans-3-bromo-2-chloro derivative afforded the trans-2-chloro-3-fluoro adduct predominantly, whereas the same reagent with the trans-2-bromo-3-chloro isomer gave nearly exclusively the cis-3-chloro-2-fluoro compound.Some mechanisms to rationalise these results are proposed.
