Biphenyl- and terphenyl-based recyclable organic trivalent iodine reagents |
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Authors: | Atsushi Moroda Hideo Togo |
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Institution: | aGraduate School of Science and Technology, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan;bDepartment of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan |
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Abstract: | Biphenyl- and terphenyl-based recyclable trivalent iodine reagents, such as 4-bromo-4′-(diacetoxyiodo)biphenyl, 4,4′-bis(diacetoxyiodo)biphenyl, 1,4-bis4-(diacetoxyiodo)phenyl]benzene, 4-bromo-4′-(hydroxy)(tosyloxy)iodo]biphenyl, 4,4′-bis(hydroxy)(tosyloxy)iodo]biphenyl, were simply prepared and their reactivities for the oxidative rearrangement of ketones to esters, TEMPO-mediated oxidation of alcohols to aldehydes or ketones, oxidative dealkylation of N-alkylsulfonamides to sulfonamides, and α-tosyloxylation of ketones were compared with p-(diacetoxyiodo)toluene and p-(hydroxy)(tosyloxy)iodo]toluene to show the same reactivities and, moreover, the biphenyl- and terphenyl-based iodoarenes formed were recovered by simple filtration of the reaction mixture in every reaction. Thus, these biphenyl- and terphenyl-based trivalent iodine reagents can be used as the recyclable reagents. |
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Keywords: | 4-Bromo-4′ -(diacetoxyiodo)biphenyl 4 4′ -Bis(diacetoxyiodo)biphenyl 1 4-Bis[4-(diacetoxyiodo)phenyl]benzene 4-Bromo-4′ -[(hydroxy)(tosyloxy)iodo]biphenyl 4 4′ -Bis[(hydroxy)(tosyloxy)iodo]biphenyl Oxidation Aldehyde Ketone Ester α -Tosyloxyketone Sulfonamide |
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