Proximity- and Chelation-Induced SNAr 1,4-Aromatic ortho-Substitution of ortho-Methoxyphenyl 2-Alkyl Ketones

被引：5

作者：

Grelier, Gwendal ^{[1
]}

Chenard, Etienne ^{[1
]}

Bueschleb, Martin ^{[1
]}

Hanessian, Stephen ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Stn Ctr Ville,CP 6128, Montreal, PQ H3C 3J7, Canada

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

aromatic substitution; biaryls; Grignard reaction in aryl ketones; steric hindrance; transition-metal-free reactions; NUCLEOPHILIC AROMATIC-SUBSTITUTION; CROSS-COUPLING REACTIONS; DIBENZOCYCLOOCTADIENE LIGNANS; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; ALKOXY GROUPS; ARYL HALIDES; ACIDS; ARYLATION;

D O I：

10.1055/s-0034-1379992

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct displacement of an o-methoxy group in o-methoxyaryl ketones with aryl, alkyl, and alkenyl Grignard reagents to provide a series of o-substituted ketones is described. Application of this reaction to the synthesis of a C-methyl analogue of a cyclooxygenase inhibitor is shown. The scope and limitations are discussed.

引用

页码：1091 / 1100

页数：10

共 46 条

[1]

Andrushko V., 2013, STEREOSELECTIVE SYNT, V1, P369

[2]

[Anonymous], 1983, SYNTHESIS

[3]

[Anonymous], 1990, J CHEM SOC CHEM COMM

[4]

[Anonymous], 1990, CHEM LETT

[5]

[Anonymous], 1991, J CHEM SOC CHEM COMM

[6] Direct Displacement of Alkoxy Groups of Vinylogous Esters by Grignard Reagents [J].

Brockway, Anthony J. ;

Gonzalez-Lopez, Marcos ;

Fettinger, James C. ;

Shaw, Jared T. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3515-3518

[7] Kinetic Diastereomer Differentiation in Au(III)- and Bi(III)-Catalyzed Benzylic Arylation: Concise and Stereocontrolled Synthesis of 2-Amino-1,1-diarylalkanes [J].

Chenard, Etienne ;

Hanessian, Stephen .

ORGANIC LETTERS, 2014, 16 (10) :2668-2671

[8]

Doucet H, 2007, CURR OPIN DRUG DISC, V10, P672

[9] THE REACTION OF PHENYL 2-METHOXY-1-NAPHTHOATE WITH GRIGNARD REAGENTS - A NEW ROUTE TO FLUORENONES [J].

FUSON, RC ;

WASSMUNDT, FW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (20) :5409-5413

[10] ortho alkylation and arylation of mesityl aryl ketones [J].

Fuson, RC ;

Speck, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2446-2448

← 1 2 3 4 5 →