ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD

被引：115
作者：
BARLUENGA, J
GONZALEZ, JM
GARCIAMARTIN, MA
CAMPOS, PJ
ASENSIO, G
机构：
[1] UNIV LA RIOJA,DEPT QUIM,E-26004 LOGRONO,SPAIN
[2] UNIV VALENCIA,FAC FARM,E-46010 VALENCIA,SPAIN
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期
关键词：
D O I：
10.1021/jo00060a020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of aromatic compounds with bis(pyridine)iodonium(I) tetrafluoroborate (IPY2BF4) in the presence of HBF4 or CF3SO3H in CH2Cl2 at room temperature furnishes monoiodo derivatives with excellent regioselectivity and yields. Use of either acid gives comparable results with activated aromatics, whereas CF3SO3H is much more effective in the iodination of deactivated aromatics.
引用
收藏
页码：2058 / 2060
页数：3
相关论文
共 39 条
  • [1] [Anonymous], 1977, ADV PHYS ORG CHEM
  • [2] IODINATION AND IODO-COMPOUNDS .3. IODINATION OF SOME AROMATIC NITRO-COMPOUNDS WITH IODINE IN 20 PERCENT OLEUM
    AROTSKY, J
    BUTLER, R
    DARBY, AC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (10): : 1480 - &
  • [3] AN EXPEDITIOUS AND GENERAL AROMATIC IODINATION PROCEDURE
    BARLUENGA, J
    GONZALEZ, JM
    GARCIAMARTIN, MA
    CAMPOS, PJ
    ASENSIO, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) : 1016 - 1017
  • [4] REGIOSELECTIVE AND STEREOSELECTIVE IODOFLUORINATION OF ALKENES WITH BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE
    BARLUENGA, J
    CAMPOS, PJ
    GONZALEZ, JM
    SUAREZ, JL
    ASENSIO, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2234 - 2237
  • [5] A SIMPLE AND GENERAL-ROUTE TO ARYL IODIDES FROM ARENES
    BARLUENGA, J
    CAMPOS, PJ
    GONZALEZ, JM
    ASENSIO, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11): : 2623 - 2624
  • [6] ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM
    BARLUENGA, J
    RODRIGUEZ, MA
    CAMPOS, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3104 - 3106
  • [7] EFFICIENT SYNTHESIS OF 2-CHLOROINDOLE, 2-BROMOINDOLE, AND 2-IODOINDOLE
    BERGMAN, J
    VENEMALM, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2495 - 2497
  • [8] BOCCHI V, 1982, SYNTHESIS-STUTTGART, P1096
  • [9] THE IODINATION OF AROMATIC SUBSTRATES ON ALUMINA
    BOOTHE, R
    DIAL, C
    CONAWAY, R
    PAGNI, RM
    KABALKA, GW
    [J]. TETRAHEDRON LETTERS, 1986, 27 (20) : 2207 - 2210
  • [10] BOVONSOMBAT P, 1992, SYNLETT, P131
1234