Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols

被引:359
作者
Peterson, KP [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/jo971268k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient procedure for the oxidation of primary and secondary allylic and benzylic alcohols to aldehydes and ketones, respectively, has been achieved using catalytic Pd(OAc)(2) in dimethyl sulfoxide (DMSO) with oxygen gas as the sole reoxidant of the palladium. Secondary substrates show increased reaction rates and improved yields with the addition of 2 equiv of NaHCO3. The reactions are free of acetal/ketal and ester byproducts.
引用
收藏
页码:3185 / 3189
页数:5
相关论文
共 57 条
[1]   PALLADIUM(II)-MEDIATED OXIDATION OF ALCOHOLS USING 1,2-DICHLOROETHANE AS PD(0) REOXIDANT [J].
AITMOHAND, S ;
HENIN, F ;
MUZART, J .
TETRAHEDRON LETTERS, 1995, 36 (14) :2473-2476
[2]   BASICITY OF THE CARBONYL GROUP .11. A RE-EXAMINATION OF THE ELECTROPHILIC SUBSTITUENT CONSTANTS FOR AMINO-SUBSTITUENTS FROM THERMODYNAMIC MEASUREMENTS [J].
AZZARO, M ;
GAL, JF ;
GERIBALDI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (04) :771-774
[3]   RUTHENIUM-CATALYZED AEROBIC OXIDATION OF ALCOHOLS VIA MULTISTEP ELECTRON-TRANSFER [J].
BACKVALL, JE ;
CHOWDHURY, RL ;
KARLSSON, U .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) :473-475
[4]   PALLADIUM-CATALYZED FORMYLATION OF ORGANIC HALIDES WITH CARBON-MONOXIDE AND TIN HYDRIDE [J].
BAILLARGEON, VP ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :452-461
[5]   SELECTIVE OXIDATION OF ALCOHOLS BY A H2O2-RUCL3 SYSTEM UNDER PHASE-TRANSFER CONDITIONS [J].
BARAK, G ;
DAKKA, J ;
SASSON, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3553-3555
[6]  
BELLOSTA V, 1993, SYNLETT, P861
[7]  
BERZELIUS JJ, 1828, J ANN, V13, P435
[8]   THE SELECTIVE OXIDATION OF PRIMARY ALCOHOLS TO ALDEHYDES BY O-2 EMPLOYING A TRINUCLEAR RUTHENIUM CARBOXYLATE CATALYST [J].
BILGRIEN, C ;
DAVIS, S ;
DRAGO, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3786-3787
[9]   HOMOGENEOUS CATALYTIC-OXIDATION OF SECONDARY ALCOHOLS TO KETONES BY MOLECULAR-OXYGEN UNDER MILD CONDITIONS [J].
BLACKBURN, TF ;
SCHWARTZ, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (05) :157-158
[10]   O-17 NMR-STUDIES ON ALKYL-SUBSTITUTED 1-TETRALONES - EFFECT OF TORSION ANGLE CHANGE AND REPULSIVE VANDERWAALS INTERACTIONS [J].
BOYKIN, DW ;
DEWPRASHAD, B ;
EISENBRAUN, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :425-429