Synthetic use of molecular iodine for organic synthesis

被引:433
作者
Togo, Hideo [1 ]
Iida, Shinpei [1 ]
机构
[1] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan
关键词
iodine; oxidation; protection; deprotection; iodocyclization; heterocycles;
D O I
10.1055/s-2006-950405
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthetic use of molecular iodine is described. Iodine is a universal oxidizing agent, especially for the oxidation of alcohols and aldehydes to esters, nitriles and amides. Further applications are the introduction of protecting groups, deprotection, iodocyclization, C-C bond formation, and formation of heterocycles. 1 Introduction 2 Oxidation of Alcohols and Aldehydes to Esters, Nitriles, Amides 3 Oxidation of Sulfides 4 Oxidation to Aromatics 5 Introduction of Protecting Groups 6 Deprotection 7 Iodocyclization 8 C-C Bond Formation 9 Formation of Heterocycles 10 Others
引用
收藏
页码:2159 / 2175
页数:17
相关论文
共 167 条
  • [1] A simple, two-step synthesis of 3-iodoindoles
    Amjad, M
    Knight, DW
    [J]. TETRAHEDRON LETTERS, 2004, 45 (03) : 539 - 541
  • [2] Iodoenolcyclisation of 2-(1,3-disubstituted-1-allyl)-1,3-dicarbonyl compounds: diastereoselective synthesis of tetrasubstituted dihydrofurans
    Antonioletti, R
    Malancona, S
    Cattaruzza, F
    Bovicelli, P
    [J]. TETRAHEDRON, 2003, 59 (10) : 1673 - 1678
  • [3] Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds
    Antonioletti, R
    Malancona, S
    Bovicelli, P
    [J]. TETRAHEDRON, 2002, 58 (43) : 8825 - 8831
  • [4] Iodine-catalysed Bohlmann-Rahtz cyclodehydration reactions
    Bagley, MC
    Glover, C
    Chevis, D
    [J]. SYNLETT, 2005, (04) : 649 - 651
  • [5] Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions
    Bandgar, BP
    Shaikh, KA
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1959 - 1961
  • [6] STUDIES ON LACTAMS .96. STEREOSPECIFIC GLYCOSYLATION VIA FERRIER REARRANGEMENT FOR OPTICAL RESOLUTION
    BANIK, BK
    MANHAS, MS
    BOSE, AK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4714 - 4716
  • [7] A remarkable iodine-catalyzed protection of carbonyl compounds
    Banik, BK
    Chapa, M
    Marquez, J
    Cardona, M
    [J]. TETRAHEDRON LETTERS, 2005, 46 (13) : 2341 - 2343
  • [8] Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition
    Banik, BK
    Fernandez, M
    Alvarez, C
    [J]. TETRAHEDRON LETTERS, 2005, 46 (14) : 2479 - 2482
  • [9] Simple synthesis of substituted pyrroles
    Banik, BK
    Samajdar, S
    Banik, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) : 213 - 216
  • [10] Enantiopure alpha-hydroxy-beta-lactams via stereoselective glycosylation
    Banik, BK
    Manhas, MS
    Bose, AK
    [J]. TETRAHEDRON LETTERS, 1997, 38 (29) : 5077 - 5080