A Metal-Free Oxidative Esterification of the Benzyl C?H Bond

被引：163

作者：

Feng, Jie ^{[1
]}

Liang, Shuai ^{[1
]}

Chen, Shan-Yong ^{[1
]}

Zhang, Ji ^{[1
]}

Fu, Song-Sen ^{[1
]}

Yu, Xiao-Qi ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 07期

基金：

美国国家科学基金会;

关键词：

benzyl C?H bond; esterification; metal-free catalyst; protected amino acids; tetrabutylammonium iodide; H BOND; FUNCTIONALIZATION; ARENES; ACTIVATION; CATALYSIS; ESTER;

D O I：

10.1002/adsc.201100920

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient metal-free oxidative esterification of benzyl C?H bonds was developed. Using tetrabutylammonium iodide as catalyst and tert-butyl hydroperoxide as co-oxidant, benzylic substrates could react smoothly with various carboxylic acids to give the esters with good to excellent yields. The method was also suitable for the O-protection of N-Boc amino acids. The reaction mechanism was primarily investigated and a radical process was proposed.

引用

页码：1287 / 1292

页数：6

共 41 条

[1] Propolis Specimens from Different Locations of Central Italy: Chemical Profiling and Gas Chromatography-Mass Spectrometry (GC-MS) Quantitative Analysis of the Allergenic Esters Benzyl Cinnamate and Benzyl Salicylate [J].

Aliboni, Andrea ;

D'Andrea, Armando ;

Massanisso, Paolo .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (01) :282-288

[2]

[Anonymous], 2008, ANGEW CHEM-GER EDIT

[3]

[Anonymous], 2009, ANGEW CHEM

[4] Direct atom-efficient esterification between carboxylic acids and alcohols catalyzed by amphoteric, water-tolerant TiO(acac)2 [J].

Chen, CT ;

Munot, YS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8625-8627

[5] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].

Chen, Long ;

Shi, Erbo ;

Liu, Zhaojun ;

Chen, Shulin ;

Wei, Wei ;

Li, Hong ;

Xu, Kai ;

Wan, Xiaobing .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089

[6] Serial ligand catalysis: A highly selective allylic C-H oxidation [J].

Chen, MS ;

Prabagaran, N ;

Labenz, NA ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6970-6971

[7] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[8]

COVELL DJ, 2008, ANGEW CHEM, V120, P6548

[9] A chiral Lewis acid strategy for enantioselective allylic C-H oxidation [J].

Covell, Dustin J. ;

White, M. Christina .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6448-6451

[10] Preparation of diphenylmethyl esters by Oxone(R) oxidation of benzophenone hydrazone [J].

Curini, M ;

Rosati, O ;

Pisani, E ;

Cabri, W ;

Brusco, S ;

Riscazzi, M .

TETRAHEDRON LETTERS, 1997, 38 (07) :1239-1240

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