Abstract
Organic halides are important synthetic intermediates in numerous reactions. They are also important due to the variety of radiohalogen-containing pharmaceuticals that have been developed in recent years [1–3]. The trialkylboranes prepared via hydroboration are conveniently converted to alkyl halides when 1 equiv of sodium hydroxide or sodium methoxide in methanol is added to a mixture of 1 mol of organoborane and 1 mol of iodine. The reaction becomes instantaneous and affords the corresponding alkyl halides. A second mole of iodine and base react similarly (Eq. 13.1) [4–6], but the third alkyl resists the reaction under these conditions.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Section 13.1
Lambrecht RM, Wolf AP (1975) In: Subramanian G, Rhodes BA, Cooper JF (eds) Radiopharmaceuticals. Society of Nuclear Medicine, New York, p 109
Heindel ND, Burns HD, Honda T, Brady LW (eds) (1978) The chemistry of radiopharmaceuticals. Masson, New York
Mazaitis JK, Gibson RE, Komai T, Eckelman WC, Francis B, Reba RC (1980) J Nucl Med 21:142
Brown HC, Rathke MW, Rogić MM (1968) J Am Chem Soc 90:5038
Brown HC, De Lue NR, Kabalka GW, Hedgecock HC Jr (1976) J Am Chem Soc 98:1290
De Lue NR, Brown HC (1976) Synthesis 114
Lane CF, Brown HC (1971) J Organomet Chem 26:C51
Brown HC, De Lue NR (1974) J Am Chem Soc 96:311
Kramer GW, Brown HC (1977) J Org Chem 42:2292
Abel EW, Gerrard W, Lappert MF (1957) J Chem Soc 112:3833
Section 13.2
Suzuki A (1982) Acc Chem Res 15:182
Negishi E, Matsushita H, Okukado N (1981) Tetrahedron Lett 2715
(a) Rand CL, Van Horn DE, Moore MW, Negishi E (1981) J Org Chem 46:4093; (b) Normant JF, Alexakis A (1981) Synthesis 841
(a) Collman JP, Hegedus LS (1980) Principles and applications of organotransition metal chemistry. University Science, Mill Valley, California; (b) Negishi E-I, (1982) Acc Chem Res 15:340; (c) Davies SG (1982) Organotransition metal chemistry: applications to organic synthesis. Pergamon, Oxford; (d) Hegedus LS (1983) Group VIII transition metals in organic synthesis. In: Scheffold R (ed) Modern synthetic methods, vol. 3. Otto Salle, Frankfurt, p 61; (e) Posner GH (1980) An introduction to synthesis using organocopper reagents. Wiley, New York, p 72; (f) Tsuji J (1980) Organic synthesis with palladium compounds. Springer, Berlin Heidelberg New York; (g) Jolly PW (1982) Nickel-catalyzed coupling of organic halides and related reactions. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry, vol. 8. Pergamon, Oxford, p 713; (h) Trost BM (1982) Organopalladium compounds in organic synthesis and in catalysis. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry, vol. 8. Pergamon, Oxford, p 799
Suzuki A, Dhillon RS (1986) Top Curr Chem 130:23
Negishi E (1980) Organometallics in organic syntheses, vol. 1. Wiley, New York
Lappert MF (1960) Angew Chem 72:36
Joy F, Lappert MF (1960) Proc Chem Soc 353
Joy F, Lappert MF, Prokai B (1966) J Organomet Chem 5:506
Lappert MF, Prokai B (1964) ibid. 384
Suzuki A (1986) Pure Appl Chem 58:629 and references cited therein
Brown HC, Kulkarni SU (1979) J Organomet Chem 168:281
Brown HC, Kulkarni SU (1979) J Org Chem 44:2422
Bhatt MV (1978) J Organomet Chem 156:221
Hara S, Dojo H, Takinami S, Suzuki A (1983) Tetrahedron Lett 24:731
Hara S, Satoh Y, Ishiguro H, Suzuki A (1983) Tetrahedron Lett 24:735
(a) Marfat A, McGuirk PR, Helquist P (1979) J Org Chem 44:3888; (b) Hooz J, Layton RB (1973) Can J Chem 51:2098
Negishi E (1982) In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry, vol. 7. Pergamon, Oxford, p 291
Jacob P III, Brown HC (1976) J Am Chem Soc 98:7832
Satoh Y, Serizawa H, Hara S, Suzuki A (1985) J Am Chem Soc 107:5225
Boeckman RK Jr, Blum DM, Ganem M, Harvey N (1977) Org Synth 58:152
Rights and permissions
Copyright information
© 2007 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
(2007). Synthesis of Halides. In: Hydroboration and Organic Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49076-0_13
Download citation
DOI: https://doi.org/10.1007/978-3-540-49076-0_13
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-49075-3
Online ISBN: 978-3-540-49076-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)