Factorial design study to access the "green" iodocyclization reaction of 2-allylphenols

Factorial design study to access the "green" iodocyclization reaction of 2-allylphenols

Author Correa, Michelle Fidelis Autor UNIFESP Google Scholar
Barbosa, Alefe Jhonatas Ramos Autor UNIFESP Google Scholar
Sato, Rie Autor UNIFESP Google Scholar
Junqueira, Luis Otavio Autor UNIFESP Google Scholar
Politi, Mario Jose Google Scholar
Rando, Daniela Goncales Autor UNIFESP Google Scholar
Fernandes, Joao Paulo dos Santos Autor UNIFESP Google Scholar
Abstract Iodocyclization of 2-allylphenols is a suitable method to access furans and dihydrofurans with adequate yields. Several methodologies to iodocyclization are reported in the literature

however, since some data about the conditions are conflicting, a more systematic approach is needed to define the best conditions. In this work, we performed a full 22 factorial design to study the influence of solvent (water or EtOH: water (1: 9) mixture) and the addition of NaHCO3 in iodine-promoted cyclization of 2-allylphenols. The results have shown water as the best solvent to be employed in the cyclization of liquid 2-allylphenols, and the presence of NaHCO 3 leads to lower yields. Several examples of 2-iodomethyl-2,3-dihydrobenzofurans preparations are reported using the optimized conditions

however, high yields are only observed when liquid 2-allylphenols were used.
Keywords dihydrobenzofuran synthesis
factorial design
green chemistry
iodocyclization
xmlui.dri2xhtml.METS-1.0.item-coverage Berlin
Language English
Sponsor Sao Paulo state (FAPESP)
Brazil government (CNPq)
CAPES
Grant number FAPESP: 2013/01875-0
FAPESP: 2013/20479-9
CNPq: 455411/2014-0
Date 2016
Published in Green Processing And Synthesis. Berlin, v. 5, n. 2, p. 145-151, 2016.
ISSN 2191-9542 (Sherpa/Romeo, impact factor)
Publisher Walter De Gruyter Gmbh
Extent 145-151
Origin http://dx.doi.org/10.1515/gps-2015-0101
Access rights Closed access
Type Article
Web of Science ID WOS:000374997600006
URI https://repositorio.unifesp.br/handle/11600/56112

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