REGIOSPECIFIC SYNTHESIS OF POLYSUBSTITUTED NAPHTHALENES AND IODOACYLNAPHTHOQUINONES VIA ZIRCONOCENE COMPLEXES OF NAPHTHALYNES

被引：41

作者：

BUCHWALD, SL

KING, SM

机构：

[1] Department of Chemistry, Massachusetts Institute of Technology, Cambridge

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 01期

关键词：

D O I：

10.1021/ja00001a037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Zirconocene complexes of substituted naphthalynes have been generated in situ and trapped with nitriles to form azametallacycles with excellent regiochemical control. These compounds can be converted into ketones, alpha-iodo ketones, and iodoacylnaphthoquinones with experimentally simple procedures.

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页码：258 / 265

页数：8

相关论文

共 30 条

[1] THE TRIMETHYLPHOSPHINE ADDUCT OF THE ZIRCONOCENE BENZYNE COMPLEX - SYNTHESIS, REACTIONS, AND X-RAY CRYSTAL-STRUCTURE [J].

BUCHWALD, SL ;

WATSON, BT ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7411-7413

[2] AN EFFICIENT ONE-POT METHOD FOR THE PREPARATION OF POLYSUBSTITUTED BENZOTHIOPHENES [J].

BUCHWALD, SL ;

QUN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2793-2797

[3] THE ZIRCONOCENE INDUCED COUPLING OF BENZYNE WITH NITRILES - SYNTHESIS, STRUCTURE AND REACTIONS OF NOVEL AZAMETALLACYCLOPENTENES [J].

BUCHWALD, SL ;

SAYERS, A ;

WATSON, BT ;

DEWAN, JC .

TETRAHEDRON LETTERS, 1987, 28 (28) :3245-3248

[4] A GENERAL-METHOD FOR THE PREPARATION OF ZIRCONOCENE COMPLEXES OF SUBSTITUTED BENZYNES - INSITU GENERATION, COUPLING REACTIONS, AND USE IN THE SYNTHESIS OF POLYFUNCTIONALIZED AROMATIC-COMPOUNDS [J].

BUCHWALD, SL ;

WATSON, BT ;

LUM, RT ;

NUGENT, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7137-7141

[5]

BUCHWALD SL, 1987, J AM CHEM SOCK, V109, P7173

[6]

BUCHWALD SL, UNPUB

[7]

BUEHLER CA, 1970, SURVEY ORGANIC SYNTH, V1, pCH12

[8] The bromination of 1 5-dihydroxy- and 1 5-diacetoxy-naphthalene, 5-methoxy1-naphthol, and 1 5-dimethoxynaphthalene [J].

Carter, AH ;

Race, E ;

Rowe, FM .

JOURNAL OF THE CHEMICAL SOCIETY, 1942, :236-239

[9]

DANHEISER RL, 1984, J ORG CHEM, V49, P1674

[10]

DRISCOLL JS, 1974, CANCER CHEMOTH REP 3, V4, P1