IMPROVED METHOD FOR SAMARIUM DIIODIDE INDUCED REDUCTIVE COUPLING REACTIONS OF ACID HALIDES

被引：39

作者：

RUDER, SM

机构：

[1] Department of Chemistry, Virginia Commonwealth University, Richmond

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)79041-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid halides are known to be reductively coupled with aldehydes and ketones in the presence of samarium diiodide to generate alpha-hydroxy ketones. Low yields of coupled product are obtained due to the competitive process of tetrahydrofuran attack on the acid chloride. This competitive reaction can be avoided and yields improved by preparation of samarium diiodide in acetonitrile.

引用

收藏

页码：2621 / 2624

页数：4

相关论文

共 17 条

[1] SYNTHESIS OF ALPHA-KETOLS MEDIATED BY DIVALENT SAMARIUM COMPOUNDS [J].

COLLIN, J ;

NAMY, JL ;

DALLEMER, F ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :3118-3122

[2] REDUCTIVE COUPLINGS OF ACID-CHLORIDES MEDIATED BY SMI2 [J].

COLLIN, J ;

DALLEMER, F ;

NAMY, JL ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1989, 30 (52) :7407-7410

[3] AN EASY COUPLING OF ACID-CHLORIDES INTO ALPHA-DIKETONES PROMOTED BY DIIODOSAMARIUM [J].

GIRARD, P ;

COUFFIGNAL, R ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1981, 22 (40) :3959-3960

[4] DIVALENT LANTHANIDE DERIVATIVES IN ORGANIC-SYNTHESIS .1. MILD PREPARATION OF SMI2 AND YBI2 AND THEIR USE AS REDUCING OR COUPLING AGENTS [J].

GIRARD, P ;

NAMY, JL ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (08) :2693-2698

[5] A NEW METHOD FOR THE HYDROXYMETHYLATION OF CARBONYL-COMPOUNDS [J].

IMAMOTO, T ;

TAKEYAMA, T ;

YOKOYAMA, M .

TETRAHEDRON LETTERS, 1984, 25 (30) :3225-3226

[6] LATHANIDES IN ORGANIC-SYNTHESIS .6. STEREOCONTROLLED CYCLIZATION REACTIONS MEDIATED BY SAMARIUM DIIODIDE [J].

MOLANDER, GA ;

ETTER, JB ;

ZINKE, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :453-463

[7] A FACILE SYNTHESIS OF BICYCLO[M.N.1]ALKAN-1-OLS - EVIDENCE FOR ORGANOSAMARIUM INTERMEDIATES IN THE SAMARIUM(II) IODIDE PROMOTED INTRAMOLECULAR BARBIER-TYPE REACTION [J].

MOLANDER, GA ;

MCKIE, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4112-4120

[8] REDUCTIVE RADICAL CYCLIZATIONS OF HALOALKENES PROMOTED BY SAMARIUM DIIODIDE - SEQUENTIAL CYCLIZATION INTERMOLECULAR CARBONYL ADDITION-REACTIONS [J].

MOLANDER, GA ;

HARRING, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6171-6176

[9] INTRAMOLECULAR REDUCTIVE COUPLING REACTIONS PROMOTED BY SAMARIUM DIIODIDE [J].

MOLANDER, GA ;

KENNY, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8236-8246

[10] LANTHANIDES IN ORGANIC-SYNTHESIS .8. 1,3-ASYMMETRIC INDUCTION IN INTRAMOLECULAR REFORMATSKY-TYPE REACTIONS PROMOTED BY SAMARIUM DIIODIDE [J].

MOLANDER, GA ;

ETTER, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6556-6558