Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoheterolysis of aryl-oxygen bonds

被引:64
作者
De Carolis, M [1 ]
Protti, S [1 ]
Fagnoni, M [1 ]
Albini, A [1 ]
机构
[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
关键词
arylation; aryl cations; aryl esters; cross-coupling; photochemistry;
D O I
10.1002/anie.200461444
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photochemical cleavage of Ar-O bonds in phenyl esters substituted with electron-donating groups offers a convenient method for the arylation of alkenes and arenes. The reaction proceeds by an SN1 mechanism via a triplet phenyl cation to form allylbenzene or biphenyl derivatives under mild conditions (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1232 / 1236
页数:5
相关论文
共 39 条
[1]   PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES [J].
BADONE, D ;
CECCHI, R ;
GUZZI, U .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6321-6323
[2]  
Bellus D., 1971, ADV PHOTOCHEM, V8, P109, DOI 10.1002/9780470133385.ch3
[3]   Allylsilanes in organic synthesis - Recent developments [J].
Chabaud, L ;
James, P ;
Landais, Y .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3173-3199
[4]   PHOTOCHEMISTRY OF IRGASAN-TRIFLATE - A SIMPLE CONVERSION OF AN AROMATIC HYDROXYL GROUP TO CHLORINE IN THE SYNTHESIS OF POLYCHLORINATED DIPHENYL ETHERS AND POLYCHLORINATED DIBENZOFURANS [J].
CHANG, YS ;
JANG, JS ;
DEINZER, ML .
TETRAHEDRON, 1990, 46 (12) :4161-4164
[5]   PENTAFLUOROPHENYLATION OF AROMATICS WITH PENTAFLUOROPHENYL PERFLUOROALKANESULFONATE AND POLYFLUOROALKANESULFONATE - A PHOTOINDUCED ELECTRON-TRANSFER CATION DIRADICAL COUPLING PROCESS [J].
CHEN, QY ;
LI, ZT .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2599-2604
[6]   Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls [J].
Dankwardt, JW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2428-2432
[7]   Aromatic allylation via diazotization: Variation of the allylic moiety and a short route to a benzazepine derivative [J].
Ek, F ;
Wistrand, LG ;
Frejd, T .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1911-1918
[8]   Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi [J].
Elhalem, E ;
Bailey, BN ;
Docampo, R ;
Ujváry, I ;
Szajnman, SH ;
Rodriguez, JB .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (18) :3984-3999
[9]   A novel α-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations [J].
Fraboni, A ;
Fagnoni, M ;
Albini, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4886-4893
[10]   Homolytic vs heterolytic paths in the photochemistry of haloanilines [J].
Freccero, M ;
Fagnoni, M ;
Albini, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) :13182-13190