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

被引：102

作者：

Chen, CT ^{[1
]}

Munot, YS ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11650, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 21期

关键词：

D O I：

10.1021/jo051337s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A diverse array of oxometallic species were examined as catalysts for a test direct condensation of benzoic acid and 2-phenylethanol in 1:1 stoichiometry. Besides group IVB MOCl2-xH(2)O and TiOX2-xH(2)O, group VB VOCl2-xTHF and group IVB TiO(acac)(2) were found to be the most efficient and water-tolerant catalysts for the test reaction. The new neutral catalytic protocol with the optimal TiO(acac)2 tolerates many stereo/electronic structural variations in both (di)acid (1 degrees-3 degrees alkyl and aryl) and (di)alcohol (1 degrees, 2 degrees alkyl, and aryl) components with high chemoselectivity.

引用

页码：8625 / 8627

页数：3

共 32 条

[1] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates [J].

Barhate, NB ;

Chen, CT .

ORGANIC LETTERS, 2002, 4 (15) :2529-2532

[2] METAL CATALYSIS IN OXIDATION BY PEROXIDES .22. A COMPARISON OF THE CATALYTIC PROPERTIES OF TITANIUM PORPHYRINATO, ALKOXO AND DIKETONATO COMPLEXES IN THE OXIDATION BY TERT-BUTYLHYDROPEROXIDE [J].

BORTOLINI, O ;

DIFURIA, F ;

MODENA, G .

JOURNAL OF MOLECULAR CATALYSIS, 1985, 33 (02) :241-244

[3] Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate [J].

Chen, CT ;

Weng, SS ;

Kao, JQ ;

Lin, CC ;

Jan, MD .

ORGANIC LETTERS, 2005, 7 (15) :3343-3346

[4] Diethylene glycol ether-linked 3,4,5-trihydroxybenzamides as triply branched dendritic anchors to CdSe/ZnS core/shell type nanoparticles: potential hydrophilic fluorescent probes [J].

Chen, CT ;

Pawar, VD ;

Munot, YS ;

Chen, CC ;

Hsu, CJ .

CHEMICAL COMMUNICATIONS, 2005, (19) :2483-2485

[5] Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species [J].

Chen, CT ;

Kuo, JH ;

Pawar, VD ;

Munot, YS ;

Weng, SS ;

Ku, CH ;

Liu, CY .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1188-1197

[6] Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species [J].

Chen, CT ;

Kuo, JH ;

Ku, CH ;

Weng, SS ;

Liu, CY .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1328-1339

[7] Site-selective DNA photocleavage involving unusual photoinitiated tautomerization of chiral tridentate vanadyl(V) complexes derived from N-salicylidene α-amino acids [J].

Chen, CT ;

Lin, JS ;

Kuo, JH ;

Weng, SS ;

Cuo, TS ;

Lin, YW ;

Cheng, CC ;

Huang, YC ;

Yu, JK ;

Chou, PT .

ORGANIC LETTERS, 2004, 6 (24) :4471-4474

[8] Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate [J].

Chen, CT ;

Kuo, JH ;

Li, CH ;

Barhate, NB ;

Hon, SW ;

Li, TW ;

Chao, SD ;

Liu, CC ;

Li, YC ;

Chang, IH ;

Lin, JS ;

Liu, CJ ;

Chou, YC .

ORGANIC LETTERS, 2001, 3 (23) :3729-3732

[9]

Chen CT, 1999, SYNLETT, P816

[10] NIOBIC ACID AS AN EFFICIENT CATALYST FOR VAPOR-PHASE ESTERIFICATION OF ETHYL-ALCOHOL WITH ACETIC-ACID [J].

CHEN, Z ;

IIZUKA, T ;

TANABE, K .

CHEMISTRY LETTERS, 1984, (07) :1085-1088

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