Direct alpha-arylation of ketones: The reaction of cyclic ketone enolates with diphenyliodonium triflate

被引：73

作者：

Ryan, JH ^{[1
]}

Stang, PJ ^{[1
]}

机构：

[1] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(97)01105-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diphenyliodonium triflate in reacts with the lithium enolates of cyclic ketones 2 (ring size = 5 - 8), in the presence of stoichiometric quantiites of copper cyanide, to afford the corresponding alpha-phenylated ketones 3 or alpha,alpha'-diphenylated ketones 4. (C) 1997 Elsevier Science Ltd.

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页码：5061 / 5064

页数：4

相关论文

共 24 条

[1] TETRAHEDRON REPORT .235. NEWER METHODS OF ARYLATION [J].

ABRAMOVITCH, RA ;

BARTON, DHR ;

FINET, JP .

TETRAHEDRON, 1988, 44 (11) :3039-3071

[2] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].

BARTON, DHR ;

FINET, JP ;

GIANNOTTI, C ;

HALLEY, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249

[3] PHENYLATION OF MONOKETONES WITH DIPHENYLIODONIUM CHLORIDE [J].

BERINGER, FM ;

DANIEL, WJ ;

GALTON, SA ;

RUBIN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4315-&

[4] AROMATIC-SUBSTITUTION BY SRN1 MECHANISM [J].

BUNNETT, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (11) :413-420

[5] DIRECT AND REGIOCONTROLLED SYNTHESIS OF ALPHA-PHENYL KETONES FROM SILYL ENOL ETHERS AND DIPHENYLIODONIUM FLUORIDE [J].

CHEN, KC ;

KOSER, GF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5764-5767

[6]

HUANG YZ, 1995, COMPREHENSIVE ORGA 2, V11, P503

[7]

KIWAJIMA I, 1982, J AM CHEM SOC, V104, P6831

[8]

KOSER GF, 1995, CHEM HALIDES PSEU SD, V2, pCH21

[9] ALPHA-PHENYLATION OF KETONES VIA TIN ENOLATES CATALYZED BY A PALLADIUM COMPLEX [J].

KOSUGI, M ;

HAGIWARA, I ;

SUMIYA, T ;

MIGITA, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (07) :344-345

[10] ARYLATION AND 1-ALKENYLATION ON ALPHA-POSITION OF KETONES VIA TRIBUTYLTIN ENOLATES CATALYZED BY PALLADIUM COMPLEX [J].

KOSUGI, M ;

HAGIWARA, I ;

SUMIYA, T ;

MIGITA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (01) :242-246