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DOI: 10.1055/s-2008-1066999
KX/H2O2 - An Efficient and Non-Polluting Halogenating Reagent in Organic Synthesis
Publication History
Publication Date:
16 April 2008 (online)
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Introduction
Halogenated organic compounds have long been known as useful synthetic intermediates, which are not only man-made, but also synthesized by a large number of different organisms. [1] Halogenated organic compounds are important components in a variety of biologically active molecules and pharmaceutical agents. [2] They form an important class of intermediates as they can be converted efficiently into other functionalities by simple chemical transformations. For example aryl, vinyl and benzylic halides serve as important precursors to organolithium [3] and Grignard [4] reagents in C-C bond formation. Aryl halides have been employed as substrates for nucleophilic aromatic substitutions [5] and for benzyne generation. [6] Additionally, both aryl [7] [8] and vinyl [9] halides have found widespread utility as substrates for a variety of cross-coupling reactions. As a result of the diverse potential applications of organic halides, the development of new regioselective, chemoselective and functional-group tolerant approaches using non-polluting reagents for the synthesis of these molecules remains an important challenge. In this context, KX/H2O2 serves as an efficient and non-polluting halogenation reagent in organic synthesis.
- 1
Gribble GW. Acc. Chem. Res. 1998, 31: 141 - 2
Butler A.Walker JV. Chem. Rev. 1993, 93: 1937 -
3a
Suryakiran N.Srikanth Reddy T.Ashalatha K.Lakshman M.Venkateswarlu Y. Tetrahedron Lett. 2006, 47: 3853 -
3b
Sotomayor N.Lete E. Curr. Org. Chem. 2003, 7: 275 - 4
Handbook of Grignard Reagents
Silverman GS.Rakita PE. Dekker; New York: 1996. - 5
Crampton MR. In Organic Reaction MechanismsKnipe AC.Watts WE. Wiley; New York: 2003. p.237 - 6
Levin RH. In Reactive Intermediates Vol. 1:Jones M.Moss RA. Wiley; New York: 1985. p.1 -
7a
Metal-Catalyzed Cross-Coupling Reactions
Dietrich F.Stang P. J. Wiley-VCH; New York: 1998. -
7b
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
7c
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 -
8a
Hassan J.Sévignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 -
8b
Hartwig JF. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-I. Wiley Interscience; New York: 2002. p.1097 -
9a
Rossi R.Carpita A.Bellina F. Org. Prep. Proced. Int. 1995, 27: 127 -
9b
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9633 - 10
Kirihara M.Ogawa S.Noguchi T.Okubo K.Monma Y.Shimizu I.Shimosaki R.Hatano A.Hirai Y. Synlett 2006, 2287 - 11
Suryakiran N.Srinivasulu M.Venkateswarlu Y. J. Sulf. Chem. 2007, 28: 345 - 12
Suryakiran N.Prabhakar P.Srikanth Reddy T.Chinni Mahesh K.Rajesh K.Venkateswarlu Y. Tetrahedron Lett. 2007, 48: 877 - 13
Mallik S.Parida KM. Catal. Commun. 2007, 8: 889 - 14
Mallik S.Parida KM.Dash SS. J. Mol. Cat. A: Chem. 2007, 261: 172 - 15
Das DP.Parida KM. J. Mol. Cat. A: Chem. 2006, 253: 70 - 16
Das DP.Parida KM. Appl. Catal., A 2006, 305: 32 - 17
Das DP.Parida KM. Catal. Commun. 2006, 7: 68 - 18
Maurya MR.Agarwal S.Bader C.Rehder D. Eur. J. Inorg. Chem. 2005, 147: 157 - 19
Narender N.Krishna Mohan KVV.Vinod Reddy R.Srinivasu P.Kulkarni SJ.Raghavan KV. J. Mol. Catal. A: Chem. 2003, 192: 73 - 20
Rothenberg G.Clark JH. Org. Proc. Res. Dev. 2000, 4: 270 - 21
Narender N.Srinivasu P.Kulkarni SJ.Raghavan KV. Synth. Commun. 2000, 30: 3669