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

被引：358

作者：

Peterson, KP ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 10期

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

页码：3185 / 3189

页数：5

共 57 条

[1] PALLADIUM(II)-MEDIATED OXIDATION OF ALCOHOLS USING 1,2-DICHLOROETHANE AS PD(0) REOXIDANT
AITMOHAND, S
HENIN, F
MUZART, J
[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
AZZARO, M
GAL, JF
GERIBALDI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (04): : 771 - 774
[3] RUTHENIUM-CATALYZED AEROBIC OXIDATION OF ALCOHOLS VIA MULTISTEP ELECTRON-TRANSFER
BACKVALL, JE
CHOWDHURY, RL
KARLSSON, U
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 473 - 475
[4] PALLADIUM-CATALYZED FORMYLATION OF ORGANIC HALIDES WITH CARBON-MONOXIDE AND TIN HYDRIDE
BAILLARGEON, VP
STILLE, JK
[J]. 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
BARAK, G
DAKKA, J
SASSON, Y
[J]. 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
BILGRIEN, C
DAVIS, S
DRAGO, RS
[J]. 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
BLACKBURN, TF
SCHWARTZ, J
[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
BOYKIN, DW
DEWPRASHAD, B
EISENBRAUN, EJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) : 425 - 429

← 1 2 3 4 5 6 →