Aerobic photocatalytic oxidation of activated benzylic and allylic alcohols to carbonyl compounds catalyzed by molecular iodine

被引：25

作者：

Farhadi, Saeid ^{[1
]}

Zabardasti, Abedien ^{[1
]}

Babazadeh, Zaynab ^{[1
]}

机构：

[1] Univ Lorestan, Dept Chem, Khorramabad 68135465, Iran

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 50期

关键词：

benzylic alcohols; photocatalytic; oxidation; aerobic; iodine;

D O I：

10.1016/j.tetlet.2006.10.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, selective and environmentally benign photocatalytic system in acetonitrile has been developed for aerobic oxidation of activated benzylic and allylic alcohols into their corresponding aldehydes and ketones without the need for a transition metal in moderate to excellent yields with a catalytic amount of iodine. Very high inter- and intramolecular chemoselectivities are observed when benzylic OH groups are oxidized in the presence of aliphatic (nonbenzylic) hydroxyls. (c) 2006 Published by Elsevier Ltd.

引用

页码：8953 / 8957

页数：5

共 50 条

[1] Green and reusable heteropolyacid catalyzed oxidation of benzylic, allylic and aliphatic alcohols to carbonyl compounds
Heravi, Majid M.
Zadsirjan, Vahideh
Bakhtiari, Khadijeh
Oskooie, Hossein A.
Bamoharram, Faterneh F.
[J]. CATALYSIS COMMUNICATIONS, 2007, 8 (03) : 315 - 318
[2] SIMPLE, COPPER(I)-CATALYZED OXIDATION OF BENZYLIC/ALLYLIC ALCOHOLS TO CARBONYL COMPOUNDS: SYNTHESIS OF FUNCTIONALIZED CINNAMATES IN ONE POT
Reddy, Alavala Gopi Krishna
Mahendar, Lodi
Satyanarayana, Gedu
[J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (14) : 2076 - 2087
[3] Catalytic aerobic oxidation of allylic alcohols to carbonyl compounds under mild conditions
Tonucci, Lucia
Nicastro, Marco
d'Alessandro, Nicola
Bressan, Mario
D'Ambrosio, Primiano
Morvillo, Antonino
[J]. GREEN CHEMISTRY, 2009, 11 (06) : 816 - 820
[4] Nitrosotetrazolium-Catalyzed Aerobic Oxidation of Alcohols to the Corresponding Carbonyl Compounds
Matsukawa, Yuta
Hirashita, Tsunehisa
Araki, Shuki
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (11) : 1359 - 1363
[5] Osmium (VI) catalyzed chemoselective oxidation of allylic and benzylic alcohols
Devari, Shekaraiah
Deshidi, Ramesh
Kumar, Manjeet
Kumar, Arvind
Sharma, Simmi
Rizvi, Masood
Kushwaha, Manoj
Gupta, Ajai Prakash
Shah, Bhahwal Ali
[J]. TETRAHEDRON LETTERS, 2013, 54 (48) : 6407 - 6410
[6] Selective Iron-Catalyzed Oxidation of Benzylic and Allylic Alcohols
Join, Benoit
Moeller, Konstanze
Ziebart, Carolin
Schroeder, Kristin
Goerdes, Dirk
Thurow, Kerstin
Spannenberg, Anke
Junge, Kathrin
Beller, Matthias
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 3023 - 3030
[7] Selective aerobic oxidation of allylic and benzylic alcohols catalyzed by N-hydroxyindole and copper(I) chloride
Shen, Shu-Su
Kartika, Vita
Tan, Ying Shan
Webster, Richard D.
Narasaka, Koichi
[J]. TETRAHEDRON LETTERS, 2012, 53 (08) : 986 - 990
[8] Gold-catalyzed benzylic oxidation to carbonyl compounds
Li, Huanrong
Li, Zhiping
Shi, Zhangjie
[J]. TETRAHEDRON, 2009, 65 (09) : 1856 - 1858
[9] Aerobic Oxidation of Benzylic Halides to Carbonyl Compounds with Molecular Oxygen Catalyzed by TEMPO/KNO2 in Aqueous Media
Liu, Qifa
Lu, Ming
Yang, Fei
Wei, Wei
Sun, Feng
Yang, Zhenbang
Huang, Sufeng
[J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (08) : 1106 - 1114
[10] CO2-Catalyzed Oxidation of Benzylic and Allylic Alcohols with DMSO
Riemer, Daniel
Mandaviya, Bhavdip
Schilling, Waldemar
Goetz, Anne Charlotte
Kuehl, Torben
Finger, Markus
Das, Shoubhik
[J]. ACS CATALYSIS, 2018, 8 (04): : 3030 - 3034

← 1 2 3 4 5 →