de Vries, J. G.: 2018 Science of Synthesis, 2017/5: Catalytic Reduction in Organic Synthesis 1 DOI: 10.1055/sos-SD-226-00191
Catalytic Reduction in Organic Synthesis 1

1.12 Catalytic Hydrodehalogenation Reactions

Weitere Informationen

Buch

Herausgeber: de Vries, J. G.

Autoren: Bonrath, W.; Cazin, C. ; Chen, Z.-P.; Dai, X.; de Vries, J. G.; Ding, K. ; Ghosh, B.; Hudson, R.; Kaneda, K. ; Li, Y.; Lv, H. ; Maleczka, Jr., R.; Medlock, J.; Mitsudome, T.; Moores, A.; Müller, M.-A.; Nahra, F. ; Nakagawa, Y.; Poechlauer, P.; Ravasio, N.; Shi, F.; Tamura, M.; Tan, X.; Tin, S.; Tomishige, K.; Zaccheria, F.; Zhang, X.; Zhou, Y.-G. ; Zimmermann, A.

Titel: Catalytic Reduction in Organic Synthesis 1

Print ISBN: 9783132406216; Online ISBN: 9783132406254; Buch-DOI: 10.1055/b-005-145236

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

 


Abstract

Hydrodehalogenation, or reductive dehalogenation, is an important organic transformation that is often used as a detoxification process in industry. A number of methods have been employed to effect this transformation in organic synthesis. Metal-catalyzed hydrodehalogenation is among the popular methods and is typically performed with molecular hydrogen or via transfer hydrogenation from other reagents. The current review highlights development in metal-catalyzed hydrodehalogenation reactions in the last 15 years, where protocols to afford spectroscopically characterized reaction products have been established.

 
  • 1 Lunin V, Lokteva E. Russ. Chem. Bull. 1996; 45: 1519
  • 2 Mohn WW, Tiedje JM. Microbiol. Rev. 1992; 56: 482
  • 3 Jefford C, Kirkpatrick D, Delay F. J. Am. Chem. Soc. 1972; 94: 8905
  • 4 Guillaumet G, Mordenti L, Caubere P. J. Organomet. Chem. 1975; 92: 43
  • 5 Boukherroub R, Chatgilialoglu C, Manuel G. Organometallics 1996; 15: 1508
  • 6 Hutchins RO, Hoke D, Keogh J, Koharski D. Tetrahedron Lett. 1969; 3495
  • 7 Kuivila HG, Menapace LW. J. Org. Chem. 1963; 28: 2165
  • 8 Knochel P, Dohle W, Gommermann N, Kneisel FF, Kopp F, Korn T, Sapountzis I, Vu VA. Angew. Chem. Int. Ed. 2003; 42: 4302
  • 9 Bailey WF, Patricia JJ. J. Organomet. Chem. 1988; 352: 1
  • 10 Alonso F, Beletskaya IP, Yus M. Chem. Rev. 2002; 102: 4009
  • 11 Sisak A, Simon OB, In The Handbook of Homogeneous Hydrogenation. de Vries JG, Elsevier CJ. EdS: Wiley-VCH Weinheim, Germany 2008; p  513
  • 12 Yin H, Wada Y, Kitamura T, Yanagida S. Environ. Sci. Technol. 2001; 35: 227
  • 13 Bunnett JF. Acc. Chem. Res. 1992; 25: 2
  • 14 Kwok WM, Zhao C, Li Y.-L, Guan X, Wang D, Phillips DL. J. Am. Chem. Soc. 2004; 126: 3119
  • 15 Douvris C, Nagaraja CM, Chen C.-H, Foxman BM, Ozerov OV. J. Am. Chem. Soc. 2010; 132: 4946
  • 16 Mandal PK, Birtwistle JS, McMurray JS. J. Org. Chem. 2014; 79: 8422
  • 17 Wullschleger CW, Gertsch J, Altmann K.-H. Chem.–Eur. J. 2013; 19: 13105
  • 18 Chan K.-P, Ling YH, Chan JL.-T, Loh T.-P. J. Org. Chem. 2007; 72: 2127
  • 19 Monguchi Y, Kume A, Hattori K, Maegawa T, Sajiki H. Tetrahedron 2006; 62: 7926
  • 20 Kannan M, Raichurkar AV, Khan FRN, Iyer PS. Bioorg. Med. Chem. Lett. 2015; 25: 1100
  • 21 Zhang Y.-M, Gu M, Ma H, Tang J, Lu W, Nan F.-J. Chin. J. Chem. 2008; 26: 962
  • 22 Bravo-Altamirano K, George KM, Frantz M.-C, LaValle CR, Tandon M, Leimgruber S, Sharlow ER, Lazo JS, Wang QJ, Wipf P. ACS Med. Chem. Lett. 2010; 2: 154
  • 23 Ramanathan A, Jimenez LS. Synthesis 2010; 217
  • 24 Arcadi A, Cerichelli G, Chiarini M, Vico R, Zorzan D. Eur. J. Org. Chem. 2004; 3404
  • 25 Sawama Y, Yabe Y, Shigetsura M, Yamada T, Nagata S, Fujiwara Y, Maegawa T, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2012; 354: 777
  • 26 Nakao R, Rhee H, Uozumi Y. Org. Lett. 2005; 7: 163
  • 27 Uozumi Y, Yamada Y. Chem. Rec. 2009; 9: 51
  • 28 Logan ME, Oinen ME. Organometallics 2006; 25: 1052
  • 29 Redwan IN, Dyrager C, Solano C, Fernández de Trocóniz G, Voisin L, Bliman D, Meloche S, Grøtli M. Eur. J. Med. Chem. 2014; 85: 127
  • 30 Bhattacharjya A, Klumphu P, Lipshutz BH. Org. Lett. 2015; 17: 1122
  • 31 Maleczka Jr. RE, Rahaim RJ, Teixeira RR. Tetrahedron Lett. 2002; 43: 7087
  • 32 Rahaim RJ, Maleczka Jr. RE. Tetrahedron Lett. 2002; 43: 8823
  • 33 Blum J, Bitan G, Marx S, Vollhardt KPC. J. Mol. Catal. 1991; 66: 313
  • 34 Li J, Zheng T, Sun H, Li X. Dalton Trans. 2013; 42: 13048
  • 35 Janni M, Peruncheralathan S. Org. Biomol. Chem. 2016; 14: 3091
  • 36 Chen J, Zhang Y, Yang L, Zhang X, Liu J, Li L, Zhang H. Tetrahedron 2007; 63: 4266
  • 37 Rasolofonjatovo E, Provot O, Hamze A, Rodrigo J, Bignon J, Wdzieczak-Bakala J, Lenoir C, Desravines D, Dubois J, Brion J.-D, Alami M. Eur. J. Med. Chem. 2013; 62: 28
  • 38 Akzinnay S, Bisaro F, Cazin CSJ. Chem. Commun. (Cambridge) 2009; 5752
  • 39 Fujita K.-I, Owaki M, Yamaguchi R. Chem. Commun. (Cambridge) 2002; 2964
  • 40 Cannon KA, Geuther ME, Kelly CK, Lin S, MacArthur AHR. Organometallics 2011; 30: 4067
  • 41 Narayanam JMR, Tucker JW, Stephenson CRJ. J. Am. Chem. Soc. 2009; 131: 8756
  • 42 Senaweera SM, Singh A, Weaver JD. J. Am. Chem. Soc. 2014; 136: 3002
  • 43 McTiernan CD, Pitre SP, Ismaili H, Scaiano JC. Adv. Synth. Catal. 2014; 356: 2819