AROMATIC IODINATION WITH THE I-2-HGX(2) COMBINATION

被引:77
作者
BACHKI, A [1 ]
FOUBELO, F [1 ]
YUS, M [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN
关键词
D O I
10.1016/S0040-4020(01)90424-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of different aromatic compounds 1a-1t with iodine and a mercury(II)-salt 2 [mercury(II) chloride, nitrate or triflate] (1:1:1 molar ratio) in dichloromethane at room temperature leads to the corresponding iodoarene 3, the obtained regiochemistry being the expected. Concerning the mercury(II) salt, the observed reactivity decreased in the series triflate>nitrate>chloride according to their ionic character. An activation of the iodine molecule by the mercury(II) salt followed by a S-E reaction with the aromatic compound is postulated as the possible mechanism.
引用
收藏
页码:5139 / 5146
页数:8
相关论文
共 91 条
[1]   NEW SYNTHESIS OF BIFLAVONES OF CUPRESSUFLAVONE SERIES [J].
AHMAD, S ;
RAZAQ, S .
TETRAHEDRON, 1976, 32 (04) :503-506
[3]   HALOGENATION WITH COPPER(II) HALIDES - SYNTHESIS OF ARYL IODIDES [J].
BAIRD, WC ;
SURRIDGE, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3436-&
[4]  
BARLEUNGA J, 1987, SYNTHESIS-STUTTGART, P582
[5]  
BARLUENGA J, 1986, SYNTHESIS-STUTTGART, P678
[6]   SYNTHESIS OF ALLYL AND DIENYL SULFONES VIA LODOSULFONYLATION OF CONJUGATED DIENES [J].
BARLUENGA, J ;
MARTINEZGALLO, JM ;
NAJERA, C ;
FANANAS, FJ ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2605-2609
[7]   AN EXPEDITIOUS AND GENERAL AROMATIC IODINATION PROCEDURE [J].
BARLUENGA, J ;
GONZALEZ, JM ;
GARCIAMARTIN, MA ;
CAMPOS, PJ ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) :1016-1017
[8]   A SIMPLE AND GENERAL-ROUTE TO ARYL IODIDES FROM ARENES [J].
BARLUENGA, J ;
CAMPOS, PJ ;
GONZALEZ, JM ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11) :2623-2624
[9]   ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD [J].
BARLUENGA, J ;
GONZALEZ, JM ;
GARCIAMARTIN, MA ;
CAMPOS, PJ ;
ASENSIO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2058-2060
[10]   POLYIODINATION ON BENZENE AT ROOM-TEMPERATURE A REGIOSELECTIVE SYNTHESIS OF DERIVATIVES [J].
BARLUENGA, J ;
GONZALEZ, JM ;
GARCIAMARTIN, MA ;
CAMPOS, PJ .
TETRAHEDRON LETTERS, 1993, 34 (24) :3893-3896