Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution

被引：57

作者：

Legros, JY ^{[1
]}

Primault, G ^{[1
]}

Toffano, M ^{[1
]}

Rivière, MA ^{[1
]}

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab Catalyse Mol,UPRESA 8075, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 04期

关键词：

D O I：

10.1021/ol991274y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Quinolylmethyl, 1-(isoquinolyl)ethyl, and 1-(quinolyl)ethyl acetates reacted with dimethylmalonate anion in the presence of a Pd(0) catalyst to give products of nucleophilic substitution and/or byproducts, depending upon the substitution pattern, The observed side reactions were reduction in the case of primary acetates and elimination or elimination/Michael-type addition sequence for secondary substrates.

引用

页码：433 / 436

页数：4

共 11 条

[1] A SYNTHESIS OF 1-VINYLISOQUINOLINE AND RELATED DERIVATIVES [J].

BOEKELHEIDE, V ;

SIEG, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (04) :587-592

[2] Arylmethyl esters as protecting groups for carboxylic, carbonic and carbamic acids: deprotection via homogeneous palladium-catalyzed hydrogenolysis [J].

Boutros, A ;

Legros, JY ;

Fiaud, JC .

TETRAHEDRON LETTERS, 1999, 40 (41) :7329-7332

[3]

BOUTROS A, IN PRESS TETRAHEDRON

[4] PALLADIUM-MEDIATED TRANSFORMATIONS OF HETEROAROMATIC TRIFLATES [J].

CRISP, GT ;

PAPADOPOULOS, S .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (02) :279-285

[5] ELECTROPHILIC AROMATIC REACTIVITIES VIA PYROLYSIS OF 1-ARYLETHYL ACETATES .12. TOTAL REACTIVITY OF ISOQUINOLINE [J].

GLYDE, E ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (15) :1783-1791

[6]

LEGROS J, UNPUB

[7] PALLADIUM-CATALYZED SUBSTITUTION OF ESTERS OF NAPHTHYLMETHANOLS, 1-NAPHTHYLETHANOLS, AND ANALOGS BY SODIUM DIMETHYL MALONATE - STEREOSELECTIVE SYNTHESIS FROM ENANTIOMERICALLY PURE SUBSTRATES [J].

LEGROS, JY ;

TOFFANO, M ;

FIAUD, JC .

TETRAHEDRON, 1995, 51 (11) :3235-3246

[8] ASYMMETRIC PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF RACEMIC 1-NAPHTHYLETHYL ESTERS [J].

LEGROS, JY ;

TOFFANO, M ;

FIAUD, JC .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1899-1902

[9]

ODA R, 1955, B I CHEM RES KYOTO U, V33, P117

[10] DETERMINATION OF ELECTROPHILIC AROMATIC REACTIVITIES VIA PYROLYSIS OF 1-ARYLETHYL ACETATES .7. TOTAL REACTIVITY OF QUINOLINE [J].

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (12) :2382-&

← 1 2 →