Electrochemical Synthesis of the Aryl α-Ketoesters from Acetophenones Mediated by KI

被引:68
作者
Zhang, Zhenlei [1 ,2 ]
Su, Jihu [3 ,4 ]
Zha, Zhenggen [1 ,2 ]
Wang, Zhiyong [1 ,2 ]
机构
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[4] Univ Sci & Technol China, Dept Modern Phys, Hefei 230026, Anhui, Peoples R China
关键词
bond-forming reactions; electrochemistry oxidation; esterification; iodine radical; oxygen; DIRECT ALDOL REACTION; KETO-ESTERS; AEROBIC OXIDATION; MOLECULAR-OXYGEN; HYDROXY ESTERS; METHYL KETONES; ACID; EFFICIENT; ACTIVATION; ALDEHYDES;
D O I
10.1002/chem.201302307
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two C-O bonds formed in one step: The oxidative coupling reaction of acetophenones with alcohol was developed by a dioxygen activation to afford α-ketoesters under electrochemical conditions. This novel transformation not only provides a simple and efficient approach to synthetize α-ketoester derivatives, but also invents a new strategy to construct a C-O bond by virtue of an anode oxidation (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:17711 / 17714
页数:4
相关论文
共 43 条
[1]   Mechanistic Insights on the Magnesium(II) Ion-Activated Reduction of Methyl Benzoylformate with Chelated NADH Peptide β-Lactam Models [J].
Aizpurua, Jesus M. ;
Palomo, Claudio ;
Fratila, Raluca M. ;
Ferron, Pablo ;
Benito, Ana ;
Gomez-Bengoa, Enrique ;
Miranda, Jose I. ;
Santos, Jose I. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) :6691-6702
[2]   ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].
ANGELASTRO, MR ;
MEHDI, S ;
BURKHART, JP ;
PEET, NP ;
BEY, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13
[3]   A study of the haloform reaction [J].
Arnold, RT ;
Buckles, R ;
Stoltenberg, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :208-210
[4]   [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights [J].
Bette, V ;
Mortreux, A ;
Savoia, D ;
Carpentier, JF .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :289-302
[5]   OXIDATION OF ALPHA-HYDROXY ESTERS TO ALPHA-KETO ESTERS USING THE DESS-MARTIN PERIODINANE REAGENT [J].
BURKHART, JP ;
PEET, NP ;
BEY, P .
TETRAHEDRON LETTERS, 1988, 29 (28) :3433-3436
[6]   Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4875-4881
[7]   Asymmetric Formal Carbonyl-Ene Reactions of Formaldehyde tert-Butyl Hydrazone with α-Keto Esters: Dual Activation by Bis-urea Catalysts [J].
Crespo-Pelna, Ana ;
Monge, David ;
Martin-Zamora, Eloisa ;
Alvarez, Eleuterio ;
Fernandez, Rosario ;
Lassaletta, Jose M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (31) :12912-12915
[8]   Organocatalyzed Anodic Oxidation of Aldehydes [J].
Finney, Eric E. ;
Ogawa, Kelli A. ;
Boydston, Andrew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12374-12377
[9]   The haloform reaction [J].
Fuson, RC ;
Bull, BA .
CHEMICAL REVIEWS, 1934, 15 (03) :275-309
[10]   Catalytic oxyalkylation of alkenes with alkanes and molecular oxygen via a radical process using N-hydroxyphthalimide [J].
Hara, T ;
Iwahama, T ;
Sakaguchi, S ;
Ishii, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6425-6431