Biphenyl- and terphenyl-based recyclable organic trivalent iodine reagents

• Published in: Tetrahedron Vol. 62; no. 52; pp. 12408 - 12414
• Main Authors: Moroda, Atsushi, Togo, Hideo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 25.12.2006; Elsevier
• Subjects: 1,4-Bis[4-(diacetoxyiodo)phenyl]benzene; 4,4′-Bis(diacetoxyiodo)biphenyl; 4,4′-Bis[(hydroxy)(tosyloxy)iodo]biphenyl; 4-Bromo-4′-(diacetoxyiodo)biphenyl; 4-Bromo-4′-[(hydroxy)(tosyloxy)iodo]biphenyl; Aldehyde; Chemistry; Chemistry, Organic; Ester; Ketone; Oxidation; Physical Sciences; Science & Technology; Sulfonamide; α-Tosyloxyketone; Ester; 4,4′-Bis(diacetoxyiodo)biphenyl; Sulfonamide; 4-Bromo-4′-[(hydroxy)(tosyloxy)iodo]biphenyl; 4,4′-Bis[(hydroxy)(tosyloxy)iodo]biphenyl; α-Tosyloxyketone; 4-Bromo-4′-(diacetoxyiodo)biphenyl; Oxidation; Aldehyde; 1,4-Bis[4-(diacetoxyiodo)phenyl]benzene; Ketone; ALPHA-TOSYLOXYLATION; ALCOHOL OXIDATION; N-ALKYLSULFONAMIDES; 4-bromo-4 '-[(hydroxy)(tosyloxy)-iodo]biphenyl; oxidation; aldehyde; CARBONYL-COMPOUNDS; MICROWAVE IRRADIATION; ketone; SONOCHEMICAL DEALKYLATION; 1,2-ARYL MIGRATION; 4,4 '-bis[(hydroxy)(tosyloxy)iodo]biphenyl; HYPERVALENT IODINE; 1,4-bis[4-(diacetoxyiodo)phenyl]benzene; sulfonamide; ester; 4-bromo-4 '-(diacetoxyiodo)biphenyl; alpha-tosyloxyketone; 4,4 '-bis(diacetoxyiodo)-biphenyl; SYNTHETIC USE; HETEROCYCLIC-COMPOUNDS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2006.09.112

Biphenyl- and terphenyl-based recyclable trivalent iodine reagents, such as 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, 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. [Display omitted]