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Efficient Oxidative Cleavage of Tetrahydrofuran‐2‐methanols to γ‐Lactones by a 2‐Iodobenzamide Catalyst in Combination with Oxone ®
Author(s) -
Yakura Takayuki,
Horiuchi Yuto,
Nishimura Yushi,
Yamada Akihiro,
Nambu Hisanori,
Fujiwara Tomoya
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500795
Subject(s) - tetrahydrofuran , chemistry , catalysis , oxidative cleavage , environmentally friendly , organic chemistry , combinatorial chemistry , medicinal chemistry , solvent , ecology , biology
Abstract An environmentally friendly oxidative cleavage of tetrahydrofuran‐2‐methanols to the corresponding γ‐lactones using a catalytic amount of 2‐iodo‐ N ‐isopropylbenzamide has been developed. The reaction of various tetrahydrofuran‐2‐methanols with the catalyst in the presence of Oxone ® (2 KHSO 5 ⋅KHSO 4 ⋅K 2 SO 4 ) as a co‐oxidant in DMF at room temperature successfully affords the corresponding lactones in good to high yields, and recovery of the catalyst is readily accomplished using a reductive work‐up. This method is notable because it enables the transformation of tetrahydrofuran‐2‐methanols to γ‐lactones under mild conditions without the use of any toxic heavy metals.