Palladium-Catalyzed Aromatic C-H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols

被引：61

作者：

Zhang, Wei ^{[1
]}

Zhang, Jian ^{[1
]}

Ren, Shaobo ^{[1
]}

Liu, Yunkui ^{[1
]}

机构：

[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 23期

关键词：

DIRECT ARYLATION; GREEN SYNTHESIS; NITROALKANES; EFFICIENT; ALKENES; FUNCTIONALIZATION; NITROARENES; DERIVATIVES; ARENES; HYDROGENATION;

D O I：

10.1021/jo502145v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C-H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.

引用

页码：11508 / 11516

页数：9

共 76 条

[1] Ruthenium-Catalyzed C-H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles [J].

Ackermann, Lutz ;

Diers, Emelyne ;

Manvar, Atul .

ORGANIC LETTERS, 2012, 14 (04) :1154-1157

[2] A warning on the use of radical traps as a test for radical mechanisms:: They react with palladium hydrido complexes [J].

Albéniz, AC ;

Espinet, P ;

López-Fernández, R ;

Sen, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11278-11279

[3] Nitroalkanes in aqueous medium as an efficient and eco-friendly source for the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans [J].

Ballini, R ;

Barboni, L ;

Giarlo, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :9173-9176

[4] Nitroalkanes as a new, convenient source of 1-acyl-2,5-dialkylbenzene derivatives, in two steps [J].

Ballini, R ;

Barboni, L ;

Bosica, G .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6261-6263

[5]

Burmistrov S. I., 1965, ZH ORG KHIM, P1000

[6] ATTEMPTED SYNTHESIS OF PHENYL NITRATE [J].

CHANEY, A ;

WOLFROM, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (08) :2998-&

[7] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

[8] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[9] FORMATION OF 4-HALO-4-NITROCYCLOHEXA-2,5-DIENONES ON NITRATION OF P-HALOPHENOLS AND P-HALOPHENYL ACETATES [J].

CLEWLEY, RG ;

CROSS, GG ;

FISCHER, A ;

HENDERSON, GN .

TETRAHEDRON, 1989, 45 (05) :1299-1310

[10] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

← 1 2 3 4 5 6 7 8 →