PENTAFLUOROPHENYLATION OF AROMATICS WITH PENTAFLUOROPHENYL PERFLUOROALKANESULFONATE AND POLYFLUOROALKANESULFONATE - A PHOTOINDUCED ELECTRON-TRANSFER CATION DIRADICAL COUPLING PROCESS

被引:40
作者
CHEN, QY
LI, ZT
机构
[1] Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
关键词
D O I
10.1021/jo00061a041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Irradiation of pentafluorophenyl perfluoro- and polyfluoroalkanesulfonates 1 with arenes, aromatic ethers, anilines, pyrroles, indoles, and phenols results in the corresponding pentafluorophenylated aromatic compounds. An electron-transfer mechanism is proposed.
引用
收藏
页码:2599 / 2604
页数:6
相关论文
共 30 条
[1]   ELECTROSYNTHESIS OF UNSYMMETRICAL BIARYLS USING A SRN1 TYPE REACTION [J].
ALAM, N ;
AMATORE, C ;
COMBELLAS, C ;
THIEBAULT, A ;
VERPEAUX, JN .
TETRAHEDRON LETTERS, 1987, 28 (49) :6171-6174
[2]  
ALBINI A, 1988, PHOTOINDUCED ELECTRO, V3, P89
[3]  
BAUMGARTNER MT, 1982, TETRAHEDRON LETT, V33, P2323
[4]  
BEUMGELMANS R, 1991, TETRAHEDRON LETT, V32, P3487
[5]   POLYFLUOROARENES .8. SOME HOMOLYTIC REACTIONS OF PENTAFLUOROIODOBENZENE [J].
BIRCHALL, JM ;
HAZARD, R ;
HASZELDI.RN ;
WAKALSKI, WW .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (01) :47-&
[6]   ARENE IMINIUM SALT ELECTRON-TRANSFER PHOTOCHEMISTRY - MECHANISTICALLY INTERESTING PHOTOADDITION PROCESSES [J].
BORG, RM ;
HEUCKEROTH, RO ;
LAN, AJY ;
QUILLEN, SL ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2728-2737
[7]   AROMATIC POLYFLUORO- COMPOUNDS .38. 1,2,3,4-TETRAFLUORODIBENZOFURAN AND SOME NUCLEOPHILIC REPLACEMENT REACTIONS [J].
BROWN, PJN ;
STEPHENS, R ;
TATLOW, JC .
TETRAHEDRON, 1967, 23 (10) :4041-&
[8]  
BUNCE NJ, 1982, J ORG CHEM, V47, P1948, DOI 10.1021/jo00349a024
[9]   PALLADIUM-CATALYZED ALKYNYL-DEHYDROXYLATION OF POLYFLUOROPHENOLS [J].
CHEN, QY ;
LI, ZT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2931-2934
[10]   PERFLUORO-SULFONIC AND POLYFLUORO-SULFONIC ACIDS .22. POLYFLUOROPHENYL PENTAFLUOROBENZENESULPHONATES AND THEIR ELECTRON-TRANSFER REACTION WITH SODIUM-IODIDE [J].
CHEN, QY ;
CHEN, MF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (07) :1071-1075