A simple and advantageous protocol for the oxidation of alcohols with, o-iodoxybenzoic acid (IBX)

被引:387
作者
More, JD [1 ]
Finney, NS [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol026427n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, user-friendly procedure for the oxidation of alcohols using IBX is described. Simply heating a solution of the alcohol in the presence of suspended IBX followed by filtration and removal of the solvent gives excellent yields of the corresponding carbonyl compounds. We illustrate this procedure with a panel of primary and secondary alcohol substrates and note that it allows recycling and reuse of the oxidant.
引用
收藏
页码:3001 / 3003
页数:3
相关论文
共 18 条
[1]  
Bunton CA, 1999, J PHYS ORG CHEM, V12, P758, DOI 10.1002/(SICI)1099-1395(199910)12:10<758::AID-POC200>3.3.CO
[2]  
2-1
[3]   Hypervalent iodine oxidants: Structure and kinetics of the reactive intermediates in the oxidation of alcohols and 1,2-diols by o-iodoxybenzoic acid (IBX) and Dess-Martin periodinane. A comparative H-1-NMR study [J].
DeMunari, S ;
Frigerio, M ;
Santagostino, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9272-9279
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]   A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].
FRIGERIO, M ;
SANTAGOSTINO, M .
TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022
[6]   OXIDATION OF ALCOHOLS WITH O-IODOXYBENZOIC ACID (IBX) IN DMSO - A NEW INSIGHT INTO AN OLD HYPERVALENT IODINE REAGENT [J].
FRIGERIO, M ;
SANTAGOSTINO, M ;
SPUTORE, S ;
PALMISANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7272-7276
[7]   A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].
Frigerio, M ;
Santagostino, M ;
Sputore, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538
[8]  
Hartmann C., 1893, CHEM BER, V26, P1727
[9]   5-AMINO-5-DEOXYRIBOSE DERIVATIVES . SYNTHESIS AND USE IN PREPARATION OF REVERSED NUCLEOSIDES [J].
LEONARD, NJ ;
CARRAWAY, KL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (04) :485-+
[10]  
Mülbaier M, 2001, ANGEW CHEM INT EDIT, V40, P4393, DOI 10.1002/1521-3773(20011203)40:23<4393::AID-ANIE4393>3.0.CO