5.5 The Wacker Process
Book
Editor: Muñiz, K.
Title: Catalytic Oxidation in Organic Synthesis
Print ISBN: 9783132012318; Online ISBN: 9783132403710; Book DOI: 10.1055/b-003-129345
1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
![](https://www.thieme-connect.de/media/10.1055-b-003-129345/thumbnails/a_214kmn.jpg)
The palladium-catalyzed Wacker process has been extended toward the oxidation of substituted α-alkenes and internal alkenes. Methods providing access to Markovnikov and anti-Markovnikov products in high selectivity are discussed.
Key words
Wacker oxidation - palladium catalysis - aldehyde-selective - ketone-selective - Markovnikov - anti-Markovnikov - oxidation - alkenes- 1 Smidt J, Hafner W, Jira R, Sedlmeier J, Sieber R, Rüttinger R, Kojer H. Angew. Chem. 1959; 71: 176
- 2 Smidt J, Hafner W, Jira R, Sieber R, Sedlmeier J, Sabel A. Angew. Chem. 1962; 74: 93 Angew. Chem. Int. Ed. Engl. 1962; 1: 80
- 9 Mitsudome T, Umetani T, Nosaka N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Angew. Chem. 2006; 118: 495 Angew. Chem. Int. Ed. 2006; 45: 481
- 11 Wang Y.-F, Gao Y.-R, Mao S, Zhang Y.-L, Guo D.-D, Yan Z.-L, Guo S.-H, Wang Y.-Q. Org. Lett. 2014; 16: 1610
- 20 Michel BW, McCombs JR, Winkler A, Sigman MS. Angew. Chem. 2010; 122: 7470 Angew. Chem. Int. Ed. 2010; 49: 7312
- 25 Wickens ZK, Morandi B, Grubbs RH. Angew. Chem. 2013; 125: 11467 Angew. Chem. Int. Ed. 2013; 52: 11257
- 27 Dong JJ, Fañanás-Mastral M, Alsters PL, Browne WR, Feringa BL. Angew. Chem. 2013; 125: 5671 Angew. Chem. Int. Ed. 2013; 52: 5561
- 29 Chu CK, Ziegler DT, Carr B, Wickens ZK, Grubbs RH. Angew. Chem. 2016; 128: 8575 Angew. Chem. Int. Ed. 2016; 55: 8435
- 32 DeLuca RJ, Edwards JL, Steffens LD, Michel BW, Qiao X, Zhu C, Cook SP, Sigman MS. J. Org. Chem. 2013; 78: 1682