Palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols

被引：24

作者：

Luo, Fang ^{[1
]}

Pan, Changduo ^{[2
]}

Cheng, Jiang ^{[1
]}

Chen, Fan ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325000, Peoples R China

[2] Wenzhou Inst Ind & Sci, Wenzhou 325000, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 33期

关键词：

OXIDATIVE ESTERIFICATION; CARBOXYLIC-ACIDS; AEROBIC OXIDATION; AROMATIC ESTERIFICATION; ATMOSPHERIC-PRESSURE; HIGHLY EFFICIENT; ALDEHYDES; ESTERS; CONVERSION; ARYL;

D O I：

10.1016/j.tet.2011.06.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols to access aryl benzoate derivatives is described. The procedure tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, fluoro and bromo groups. Thus, it represents a practically alternative method to access aryl benzoate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5878 / 5882

页数：5

共 82 条

[11] STEREOSPECIFIC TOTAL SYNTHESIS OF DL-C18 CECROPIA JUVENILE HORMONE [J].

COREY, EJ ;

KATZENELLENBOGEN, JA ;

GILMAN, NW ;

ROMAN, SA ;

ERICKSON, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5618-+

[12] ONE-STEP CONVERSION OF PRIMARY ALCOHOLS IN THE CARBOHYDRATE SERIES TO THE CORRESPONDING CARBOXYLIC TERT-BUTYL ESTERS [J].

COREY, EJ ;

SAMUELSSON, B .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24) :4735-4735

[13] NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS [J].

COREY, EJ ;

GILMAN, NW ;

GANEM, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5616-&

[14] Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer-Villiger oxidations [J].

Corma, A ;

Nemeth, LT ;

Renz, M ;

Valencia, S .

NATURE, 2001, 412 (6845) :423-425

[15] Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids [J].

Dai, Jian-Jun ;

Liu, Jing-Hui ;

Luo, Dong-Fen ;

Liu, Lei .

CHEMICAL COMMUNICATIONS, 2011, 47 (02) :677-679

[16] Acetylation and benzoylation of various aromatics on sulfated zirconia [J].

Deutsch, J ;

Trunschke, A ;

Müller, D ;

Quaschning, V ;

Kemnitz, E ;

Lieske, H .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 207 (01) :51-57

[17] One-pot oxidative esterification and amidation of aldehydes [J].

Ekoue-Kovi, Kekeli ;

Wolf, Christian .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) :6302-6315

[18] Peroxovanadium-catalyzed oxidative esterification of aldehydes [J].

Gopinath, R ;

Barkakaty, B ;

Talukdar, B ;

Patel, BK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2944-2947

[19] V2O5-H2O2:: a convenient reagent for the direct oxidation of acetals to esters [J].

Gopinath, R ;

Paital, AR ;

Patel, BK .

TETRAHEDRON LETTERS, 2002, 43 (29) :5123-5126

[20] A catalytic oxidative esterification of aldehydes using V2O5-H2O2 [J].

Gopinath, R ;

Patel, BK .

ORGANIC LETTERS, 2000, 2 (05) :577-579

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