Gold catalysis:: Proof of arene oxides as intermediates in the phenol synthesis

被引:171
作者
Hashmi, ASK
Rudolph, M
Weyrauch, JP
Wöelfle, M
Frey, W
Bats, JW
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
[2] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany
关键词
arene oxides; density functional calculations; gold; homogeneous catalysis; N ligands;
D O I
10.1002/anie.200462672
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) An elusive intermediate in the gold-catalyzed phenol synthesis was elucidated by modifying the energy profile of this process. Thus, the use of a ligand based on 2-hydroxymethylpyridine enabled the first observation of the intermediate arene oxide, which can be enriched to account for up to 80% of the material in the reaction mixture at room temperature (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2798 / 2801
页数:4
相关论文
共 30 条
[1]  
Belen'kll L. I., 1996, COMPREHENSIVE HETERO, V9, P45
[2]   The changing face of arene oxide oxepine chemistry [J].
Boyd, DR ;
Sharma, ND .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (04) :289-&
[3]   OXYGEN WALK AS A COMPLEMENTARY OBSERVATION TO NIH SHIFT [J].
BRUICE, PY ;
KASPEREK, GJ ;
BRUICE, TC ;
YAGI, H ;
JERINA, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (05) :1673-1674
[4]   DISPLACEMENT OF PYRIDINE-2-METHANOL FROM DICHLORO(PYRIDINE-2-METHANOLATO)GOLD(III) IN ACIDIC SOLUTION - RING-OPENING AT OXYGEN [J].
CANOVESE, L ;
CATTALINI, L ;
MARANGONI, G ;
TOBE, ML .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (04) :731-735
[5]   COMPLEXES OF GOLD(III) WITH MONONEGATIVE BIDENTATE N,O-LIGANDS [J].
DAR, A ;
MOSS, K ;
COTTRILL, SM ;
PARISH, RV ;
MCAULIFFE, CA ;
PRITCHARD, RG ;
BEAGLEY, B ;
SANDBANK, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (12) :1907-1913
[6]   PI-FACIAL STEREOSELECTIVITY IN THE DIELS-ALDER REACTIONS OF BENZENE OXIDES [J].
GILLARD, JR ;
NEWLANDS, MJ ;
BRIDSON, JN ;
BURNELL, DJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (09) :1337-1343
[7]   APPLICATIONS OF C-13 RESONANCE SPECTROSCOPY .4. SPECTRA OF OXEPINES AND BENZENES OXIDES AND INFLUENCE OF OXYGEN ON CHEMICAL-SHIFT OF C-13 [J].
GUNTHER, H ;
JIKELI, G .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (06) :1863-1880
[8]   HYDROXYLATION-INDUCED MIGRATION - NIH SHIFT [J].
GUROFF, G ;
DALY, JW ;
JERINA, DM ;
RENSON, J ;
WITKOP, B ;
UDENFRIE.S .
SCIENCE, 1967, 157 (3796) :1524-&
[9]  
Hashmi A. S. K., 2004, ANGEW CHEM, V116, P6707, DOI DOI 10.1002/ANGE.200460232
[10]   Gold catalysis: On the phenol synthesis [J].
Hashmi, ASK ;
Frost, TM ;
Bats, JW .
ORGANIC LETTERS, 2001, 3 (23) :3769-3771