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

Green Processing and Synthesis

article

Michelle Fidelis Corrêa¹  Álefe Jhonatas Ramos Barbosa¹  Rie Sato¹  Luis Otávio Junqueira¹  Mário José Politi²  Daniela Gonçales Rando¹  João Paulo dos Santos Fernandes¹ 

[1] Department of Exact and Earth Sciences, Federal University of São Paulo;Institute of Chemistry, Department of Biochemistry, University of São Paulo

关键词: dihydrobenzofuran synthesis;    factorial design;    green chemistry;    iodocyclization;   

DOI  :  10.1515/gps-2015-0101

来源: De Gruyter

【 摘 要 】

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 2 2 factorial design to study the influence of solvent (water or EtOH:water (1:9) mixture) and the addition of NaHCO 3 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.

【 授权许可】

CC BY