5.4 Halogenation and Halocyclization of Alkenes
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
Halogenated compounds are of high importance in many disciplines, even beyond chemistry. The unique properties that can be traced back to the halogen atom make the development of methods for selectively installing carbon—halogen bonds a rewarding goal. This chapter provides an overview of effective methods for the chemo-, regio-, and, in particular, stereoselective formation of C—X bonds using different oxidative approaches.
Key words
halogenation - halocyclization - dihalogenation - organocatalysis - hypervalent iodine - ion pairing - phosphoric acids - C3-symmetric trisimidazolines - amino ureas - Lewis base catalysis - hydrogen bonding - carbamates - thiocarbamates - dimeric cinchona alkaloids - Lewis acid catalysis - titanium - scandium- 6 Ulmer A, Stodulski M, Kohlhepp SV, Patzelt C, Pöthig A, Bettray W, Gulder T. Chem.–Eur. J. 2015; 21: 1444
- 16 Brown RS, Nagorski RW, Bennet AJ, McClung RED, Aarts GHM, Klobukowski M, McDonald R, Santarsiero BD. J. Am. Chem. Soc. 1994; 116: 2448
- 43 Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12924
- 44 Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H. Angew. Chem. Int. Ed. 2010; 49: 9174
- 53 Sawamura Y, Ogura Y, Nakatsuji H, Sakakura A, Ishihara K. Chem. Commun. (Cambridge) 2016; 52: 6068
- 78 Chen Z.-M, Zhang Q.-W, Chen Z.-H, Li H, Tu Y.-Q, Zhang F.-M, Tian J.-M. J. Am. Chem. Soc. 2011; 133: 8818
- 81 El-Qisairi AK, Qaseer HA, Katsigras G, Lorenzi P, Trivedi U, Tracz S, Hartman A, Miller JA, Henry PM. Org. Lett. 2003; 5: 439
- 92 Huang W.-S, Chen L, Zheng Z.-J, Yang K.-F, Xu Z, Cui Y.-M, Xu L.-W. Org. Biomol. Chem. 2016; 14: 7927