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fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
Publisher: Arkat USA Inc
Languages: English
Types: Article
Subjects: QD
Keith received an MSc in 1969 and a PhD in 1971 for his work in this area and was awarded a Royal Society European Exchange Fellowship to take up a postdoctoral\ud research position with Professor Albert Eschenmoser at the ETH in Zürich, Switzerland, where he contributed to a project on chlorophyll derivatives. While Keith was in\ud Switzerland, Andrew Pelter moved to Swansea University to take up a position as Professor of Organic Chemistry and a lectureship became available there. Keith was appointed to the position from October 1972 and rejoined his ollaboration with Pelter on organoboron chemistry. Among other reactions, they introduced methods for syntheses of unsymmetrical\ud conjugated diynes from the corresponding dialkyldialkynylborates, of secondary and tertiary alcohols from reactions of trialkylboranes with bis(phenylthio)alkyllithiums8 or 2-lithio-2-\ud alkylbenzodithioles, of N-substituted sulfonamides, and of dialkylbromoboranes.
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    • 1. Pelter, A.; Levitt, T.; Smith, K. The Reaction of trisalkylthioboranes with carboxylic acids; a new thioester synthesis. J. Chem. Soc., Chem. Commun. 1969, 435. Full paper: Pelter, A.; Levitt, T. E.; Smith, K.; Jones, A. Synthesis of thioesters by reactions of carboxylic acids with tris(ethylthio)borane. J. Chem. Soc., Perkin Trans. 1 1977, 1672.
    • 2. Pelter, A.; Hutchings, M. G.; Smith, K. The reactions of electrophilic reagents with trialkylcyanoborates: some new efficient ketone syntheses. J. Chem. Soc., Chem. Commun. 1970, 1529.
    • 3. Pelter, A.; Hutchings, M. G.; Smith, K. 1,1,2-Trimethylpropyldialkylcyanoborates as intermediates for the synthesis of symmetrical, unsymmetrical, functionalised, and cyclic ketones. J. Chem. Soc., Chem. Commun. 1971, 1048. Full paper: Pelter, A.; Smith, K.; Hutchings, M. G.; Rowe, K. The chemistry of organoborates. Part I. New, high yield ketone syntheses by reaction of trialkylcyanoborates with acylating agents or N-phenylbenzimidoyl chloride. J. Chem. Soc., Perkin Trans. 1 1975, 129.
    • 4. Pelter, A.; Hutchings, M. G.; Smith, K. Trialkylcyanoborates as intermediates in a new conversion of trialkylboranes into trialkylcarbinols. J. Chem. Soc., Chem. Commun. 1971, 1048. Full Paper: Pelter, A.; Hutchings, M. G.; Rowe, K.; Smith, K. The chemistry of organoborates. Part II. High yield syntheses of trialkylmethanols by the cyanoborate process. J. Chem. Soc., Perkin Trans.1 1975, 138.
    • 5. Pelter, A.; Hutchings, M. G.; Smith, K. Stereochemistry and order of the three alkyl migrations in the cyanoborate process. J. Chem. Soc., Chem. Commun. 1973, 186. Full paper: Pelter, A.; Hutchings, M. G.; Smith, K. Williams, D. J. The chemistry of organoborates. Part IV. Stereochemistry and relative migratory aptitudes of alkyl groups in the cyanoborate process. J. Chem. Soc., Perkin Trans. 1 1975, 145.
    • 6. Isenring, H.-P.; Zass, E.; Smith, K.; Falk, H.; Luisier, J.-L.; Eschenmoser, A. Uber enolisierte derivate der chlorophyllreihe. 132-Desmethoxycarbonyl-173-desoxy-132,173- cyclochlorophyllid a-enol und eine methode zur einfuhrung von magnesium in porphinoide ligandsysteme unter milden bedingungen. Helv. Chim. Acta 1975, 58, 2357.
    • 7. Pelter, A.; Hughes, R. J.; Smith, K.; Tabata, M. A new synthesis of unsymmetrical conjugated diynes. Tetrahedron Lett. 1976, 17, 4385.
    • 8. Hughes, R. J.; Pelter, A.; Smith, K.; Negishi, E.; Yoshida, T. Preparation of secondary alcohols by reaction of trialkylboranes with bis(phenylthio)methyllithium. Tetrahedron Lett. 1976, 17, 87; Hughes, R. J.; Ncube, S.; Pelter, A.; Smith, K.; Negishi, E.; Yoshida, T. Synthesis of secondary and tertiary alcohols by reactions of trialkylboranes with acyl carbanion equivalents. J. Chem. Soc., Perkin Trans. 1 1977, 1172.
    • 9. Ncube, S.; Pelter, A.; Smith, K. Improved synthesis of tertiary alcohols from reactions of organoboranes with 2-lithio-1,3-benzodithioles. Tetrahedron Lett. 1979, 20, 1895.
    • 10. Jigajinni, V. B.; Pelter, A.; Smith, K. Reactions of organoboranes with chloramine-T and its analogues; synthesis of N-substituted sulphonamides. Tetrahedron Lett. 1978, 19, 181.
    • 11. Pelter, A.; Rowe, K.; Sharrocks, D. N.; Smith, K.; Subrahmanyam, C. Reaction of higher dialkyl(methylthio)boranes with bromine: a new synthesis of dialkylbromoboranes. J. Chem. Soc., Dalton Trans. 1976, 2087.
    • 12. Smith, K.; Swaminathan, K. Reaction of dibutylchloroborane with sodium-potassium alloy followed by benzoyl chloride. A reinvestigation and discussion. J. Chem. Soc., Dalton Trans. 1976, 2297.
    • 13. Fletcher, A. S.; Paget, W. E.; Smith, K.; Swaminathan, K.; Beynon, J. H.; Morgan, R. P.; Bozorgzadeh, M.; Haley, M. J. Novel organoborane compound type from the reaction of diphenylbromoborane with di-isopropylcarbamoyl-lithium. J. Chem. Soc., Chem. Commun. 1979, 347.
    • 14. Brown, H. C.; Hubbard, J. L.; Smith, K. Carbonylation of organoboranes in the presence of potassium triisopropoxyborohydride; a superior reagent for the synthesis of aldehydes or primary alcohols from alkenes via hydroboration - carbonylation. Synthesis 1979, 701 Hubbard, J. L.; Smith, K. Hydride-induced carbonylation of organoboranes. Evidence that all complex metal hydrides evaluated react by way of alkali metal trialkylborohydride intermediates. J. Organomet. Chem. 1984, 276, C41.
    • 15. Pelter, A.; Smith, K. Organic Boron Compounds, Comprehensive Organic Chemistry, Pergamon, Oxford, 1979, 3, 689-940.
    • 16. Brown, H. C.; Smith, K. Hydroboration, Kirk-Othmer Concise Encyclopedia of Chemical Technology, Wiley, New York, 1985, 612-615.
    • 17. Smith, K. (Editor) Boron Compounds, Dictionary of Organometallic Compounds. Chapman and Hall, 1984, 1, 204-431.
    • 18. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents. Academic, London, 1988.
    • 19. Smith, K. Organoboron Chemistry. Schlosser, M. (Ed) Organometallics in Synthesis: A Manual., Wiley, Chichester, 1994, 461-508; 2nd edition, 2004, 465-533.
    • 20. See, for example: Maddocks, P. J.; Pelter, A.; Rowe, K.; Smith, K.; Subrahmanyam, C. Reactions of dialkylbromoboranes with alkali metal hydrides in the presence of alkenes. Synthesis of 'mixed' trialkylboranes (RA2RBB). J. Chem. Soc., Perkin Trans. 1 1981, 653; Pelter, A.; Smith, K.; Jones, K. D. Allene synthesis using boron-stabilised alkenyl carbanions. J. Chem. Soc., Perkin Trans. 1 1992, 747; Smith, K.; Pelter A.; Jin, Z. Hindered organoboron groups in organic chemistry. 26. The synthesis and properties of 2,4,6-trimethylphenylborane (mesitylborane), a stable alternative to thexylborane. Angew. Chem. 1994, 106, 913; Angew. Chem. Int. Ed. Engl. 1994, 33, 851; Smith, K.; El-Hiti, G. A.; Hou, D.; DeBoos, G. A. Preparation and use of sterically hindered organobis(2,4,6- triisopropylphenyl)hydroborates and their polystyrene derivatives for diastereoselective reduction of ketones. J. Chem. Soc., Perkin Trans. 1 1999, 2807.
    • 21. Smith, K.; Balakit, A. A.; Pardasani, R. T.; El-Hiti, G. A. New polymeric sulfide-borane complexes: convenient hydroborating and reducing reagents. J. Sulfur Chem. 2011, 32, 287.
    • 22. Fletcher, A. S.; Smith K.; Swaminathan, K. Generation of di-isopropylcarbamoyl-lithium from N,N-di-isopropylformamide and t-butyl-lithium. Syntheses of -hydroxy and -oxoamides. J. Chem. Soc., Perkin Trans. 1, 1977, 1881.
    • 23. Davies, J. S.; Smith, K.; Turner, J. R.; Gymer, G. Novel heterocyclic systems. Part 3. The first dipyrido-oxathiin, and new routes to a dipyridodioxin and a dipyridothiin. Tetrahedron Lett. 1979, 20, 5035.
    • 24. Morgan, P. J.; Smith, K. Potentiality of seaweed as a resource: analysis of the pyrolysis products of Fucus serratus. Analyst (London) 1978, 103, 1053.
    • 25. Brown, C. A.; Miller, R. D.; Lindsay, C. M.; Smith, K. Generation of 2-lithio-2- (methylthio)-1,3-benzodithioles, new carboxyl carbanion equivalents, and their application to the synthesis of unsymmetrical hexathioorthooxalates. Tetrahedron Lett. 1984, 25, 991.
    • 26. Smith, K.; Lindsay, C. M.; Pritchard, G. J. Directed lithiation of arenethiols. J. Am. Chem. Soc. 1989, 111, 665.
    • 27. See, for example: Smith, K.; Pritchard, G. J. Carbonylation of doubly lithiated N-pivaloylanilines. A novel approach to dioxindoles via intramolecular trapping of aromatic acyllithiums. Angew. Chem. 1990, 102, 298; Angew Chem. Int. Ed. Engl. 1990, 29, 282; Smith, K.; El-Hiti, G. A.; Hawes, A. C. A novel procedure for the formation of isatins via carbonylation of lithiated N'-aryl-N,N-dimethylureas. Synlett 1999, S1, 945; Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums. J. Chem. Soc., Perkin Trans. 1 1999, 2299.
    • 28. Smith, K.; Lindsay, C. M.; Morris, I. K.; Matthews, I.; Pritchard, G. J. The synthesis of 2-substituted thiazolo[5,4-c]pyridines via directed metalation. Sulfur Lett. 1994, 17, 197.
    • 29. Smith, K.; Anderson, D.; Matthews, I. A convenient synthesis of 2-substituted thiazolo[4,5-b]pyridines via directed metalation. Sulfur Lett. 1995, 18, 79.
    • 30. Smith, K.; Hou, D. A superior procedure for generation of substituted benzyllithiums from the corresponding chlorides. J. Chem. Soc., Perkin Trans. 1 1995, 185.
    • 31. Smith, K.; Hou, D. A general and efficient method for preparation of organic sulfonic acids by insertion of sulfur trioxide into the metal-carbon bond of organolithiums. J. Org. Chem. 1996, 61, 1530.
    • 32. Jigajinni, V. B.; Paget, W. E.; Smith, K. The synthesis of alkyl chlorides via reaction of trialkylboranes with dichloramine-T or N,N-dichlorourethane. J. Chem. Res. (S) 1981, 376.
    • 33. Smith, K.; Butters, M.; Paget, W. E.; Nay, B. New reagent systems for electrophilic chlorination of aromatic compounds: organic chlorine-containing compounds in the presence of silica. Synthesis 1985, 1155.
    • 34. Smith, K.; Butters, M.; Paget, W. E.; Goubet, D.; Fromentin, E.; Nay, B. Highly selective monochlorination of aromatic compounds under mild conditions by tert-butyl hypochlorite in the presence of zeolites. Green Chem. 1999, 1, 83.
    • 35. Mistry, A. G.; Smith, K.; Bye, M. R. A superior synthetic method for the bromination of indoles and benzimidazoles. Tetrahedron Lett. 1986, 27, 1051; Smith, K.; James, D. M.; Mistry, A. G.; Bye, M. R.; Faulkner, D. J. A new method for bromination and polybromination of carbazoles, -carbolines and iminodibenzyls by using N-bromosuccinimide and silica gel. Tetrahedron 1992, 48, 7479.
    • 36. Smith, K.; El-Hiti, G. A.; Bahzad, D.; Hammond, M. E. W.; Li, Z.; Siquet, C. Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds using bromine in the presence of reusable zeolites. J. Chem. Soc., Perkin Trans. 1 2000, 2745.
    • 37. Smith, K.; Pollaud, G. M.; Matthews, I. Synthesis of 1-aryl-2-alkenes and 1-arylalkanes via Friedel-Crafts alkylation of aromatic substrates with allylic alcohols over solid acid catalysts. Green Chem. 1999, 1, 75.
    • 38. See, for example: Smith, K.; El-Hiti, G. A.; Jayne, A.; Butters, M. Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers. Org. Biomol. Chem. 2003, 1, 1560; Smith, K.; El-Hiti, G. A.; Jayne, A.; Butters, M. Acylation of aromatic ethers over solid acid catalysts: scope of the reaction with more complex acylating agents. Org. Biomol. Chem. 2003, 1, 2321.
    • 39. Smith, K.; Ewart, G. M.; El-Hiti, G. A.; Randles, K. R. Study of regioselective methanesulfonylation of simple aromatics with methanesulfonic anhydride in the presence of zeolite catalysts. Org. Biomol. Chem. 2004, 2, 3150.
    • 40. DeLaude, L.; Laszlo, P.; Smith, K. Heightened selectivity in aromatic substitutions by the use of solid supports and catalysts. Acc. Chem. Res. 1993, 26, 607-613; Smith, K.; Musson, A.; DeBoos, G. A. A novel method for the nitration of simple aromatic compounds. J. Org. Chem. 1998, 63, 8448.
    • 41. Smith K. (Editor) Solid Supports and Catalysts in Organic Synthesis. Ellis Horwood, Chichester, 1992.
    • 42. Davies, J. S.; Smith, K.; Turner, J. R. Novel heterocyclic systems. Part 4. A simple, convenient synthesis of 3-hydroxypyridine-2-thione, and the preparation of two novel tricyclic betaines. Tetrahedron Lett. 1980, 21, 2191.
    • 43. See, for example: Smith, K.; Matthews, I.; Hulme, N. M.; Martin, G. E. Novel heterocyclic systems. Part 21. Synthesis of 3-hydroxypyridine-2(1H)-selone and its application in the synthesis of 1-azaphenoxaselenine and its substituted derivatives. J. Chem. Soc., Perkin Trans. 1. 1986, 2075; Matthews, I.; Smith, K.; Martin, G. E. Novel heterocyclic systems. Part 28. Preparation and characterization of the 1,6-, 1,7-, 1,8- and 1,9-diazaphenoxaselenines: an unexpected divergence between closely related sulphur and selenium systems. J. Chem. Soc., Perkin Trans. 1. 1987, 2839.
    • 44. Smith, K.; Hammond, M. E. W.; James, D. M.; Ellison, I. J.; Hutchings, M. G. Regiospecific synthesis of 1-substituted 1,2,4-triazoles by reaction of 1,2,4-triazole with aldehydes. Chem. Lett. 1990, 351; Smith, K.; Small, A.; Hutchings, M. G. Regiospecific synthesis of -alkoxy- and -alkylthio-1-alkyl-1,2,4-triazoles from aldehydes and glyoxals. Synlett 1991, 485.
    • 45. Lindsay, C. M.; Smith, K.; Brown, C. A.; Betterton-Cruz, K. Facile synthesis of unsymmetrical benzotetrathiafulvalenes via cleavage of the corresponding hexathioorthooxalates. Tetrahedron Lett. 1984, 25, 995.
    • 46. See, for example: Smith, K.; El-Hiti, G. A.; Abdo, M. A.; Abdel-Megeed, M. F. Regiospecific electrophilic substitution of aminoquinazolinones: direct lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methyl-4(3H)-quinazolinones. J. Chem. Soc., Perkin Trans. 1 1995, 1029; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. Lithiation of 3-(acylamino)-2-unsubstituted-, 3-(acylamino)-2-ethyl- and 3-(acylamino)-2- propyl-4(3H)-quinazolinones: convenient syntheses of more complex quinazolinones. J. Org. Chem. 1996, 61, 647; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. Lithiation of 2-alkyl-3-amino- and 2-alkyl-3-methylamino-4(3H)-quinazolinones. J. Org. Chem. 1996, 61, 656; Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)-ones: application in synthesis. Synthesis 2004, 2121.
    • 47. Smith, K.; El-Hiti, G. A.; Hamilton, A. Unexpected formation of substituted anilides via reactions of trifluoroacetanilides with lithium reagents. J. Chem. Soc., Perkin Trans. 1 1998, 4041.
    • 48. See, for example: Smith, K.; El-Hiti, G. A.; Shukla, A. P. Variation in site of lithiation with ring substitution of N'-aryl-N,N-dimethylureas: application in synthesis. J. Chem. Soc., Perkin Trans. 1 1999, 2305; Smith, K.; Barratt, M. L. 5-Substitution of 3-methylthiophene via highly selective lithiation. J. Org. Chem. 2007, 72, 1031; Smith, K.; El-Hiti, G. A.; Hegazy, A. S. Unexpected variations in sites of lithiation of N-(2-methoxybenzyl)pivalamides. Synlett 2009, 2242; Smith, K.; El-Hiti, G. A.; Hegazy, A. S.; Fekri, A.; Kariuki, B. M. Variation in sites of lithiation of substituted N-benzylpivalamides and N'-benzyl-N,N-dimethylureas: application in synthesis. Arkivoc 2009, (xiv), 266; Smith, K.; El-Hiti, G. A.; Hegazy, A. S. Lateral lithiation of N'-(2-methylbenzyl)-N,N-dimethylurea and N'-(2-methylbenzyl)-pivalamide: synthesis of tetrahydroisoquinolines. Synthesis 2010, 1371.
    • 49. Smith, K.; El-Hiti, G. A.; Hegazy, A. S. One-pot synthesis of substituted isoindolin-1- ones via lithiation and substitution of N'-benzyl-N,N-dimethylureas. Chem. Commun. 2010, 46, 2790.
    • 50. Smith, K.; Liu, C.-H.; El-Hiti, G. A. A Novel supported Katsuki-type (salen)Mn complex for asymmetric epoxidation. Org. Biomol. Chem. 2006, 4, 917.
    • 51. Smith, K.; Almeer, S.; Black, S. J. para-Selective nitration of halogenobenzenes using a nitrogen dioxide-oxygen-zeolite system. Chem. Commun. 2000, 1571; Smith, K.; Almeer, S.; Peters, C. Regioselective mononitration of aromatic compounds by zeolite/dinitrogen tetroxide/air in a solvent-free system. Chem. Commun. 2001, 2748.
    • 52. Smith, K.; Gibbins, T.; Millar, R. W.; Claridge, R. P. A Novel method for the nitration of deactivated aromatic compounds. J. Chem. Soc., Perkin Trans. 1 2000, 2753.
    • 53. Smith, K.; Ajarim, M. D.; El-Hiti, G. A. Regioselective nitration of deactivated monosustituted benzenes using acyl nitrates over reusable zeolite catalysts. Catal. Lett. 2010, 134, 270.
    • 54. Smith, K.; El-Hiti, G. A.; Al-Shamali, M. Rearrangement of epoxides to carbonyl compounds in the presence of reusable acidic zeolite catalysts under mild conditions. Catal. Lett. 2006, 109, 77; Smith, K.; El-Hiti, G. A.; Matthews, I.; Al-Shamali, M.; Watson, T. Rearrangement of epoxides to allylic alcohols in the presence of reusable basic resins. Catal. Lett. 2009, 128, 101.
    • 55. Smith, K.; Roberts, S. D.; El-Hiti, G. A. Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts. Org. Biomol. Chem. 2003, 1, 1552.
    • 56. Smith, K.; El-Hiti, G. A. Regioselective control of electrophilic aromatic substitution reactions. Curr. Org. Synth. 2004, 1, 253; Smith, K.; El-Hiti, G. A. Regioselective electrophilic aromatic substitution reactions over reusable zeolites. Curr. Org. Chem. 2006, 10, 1603; Smith, K.; Evans, D. A.; El-Hiti, G. A. Role of modern chemistry in sustainable arable agricultural products “in Sustainable Agriculture I”. eds. Pollock, C.; Pretty, J.; Crute, I.; Leaver, C.; Dalton, H. Phil. Trans. R. Soc. B 2008, 363, 623; Smith, K.; El-Hiti, G. A. Use of zeolites for greener and more para-selective electrophilic aromatic substitution reactions. Green Chem. 2011, 13, 1579.
    • 57. See, for example: Batmanghelich, S.; Woodhead, J. S.; Smith, K.; Weeks, I. Synthesis and chemiluminescent evaluation of a series of phenyl-N-alkylacridinium-9-carboxylates. J. Photochem. Photobiol., A: Chem. 1991, 56, 249; Smith, K.; Li, Z.; Yang, J.-J.; Weeks, I.; Woodhead, J. S. Synthesis and properties of novel chemiluminescent biological probes: substituted 4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9- carboxylate trifluoromethanesulfonate. J. Photochem. Photobiol. A: Chem. 2000, 132, 181.
    • 58. See, for example: Brown, R. C.; Li, Z.; Rutter, A. J.; Mu, X.; Weeks, O. H.; Smith, K.; Weeks, I. Development and application of a novel acridinium ester for use as a chemiluminescent emitter in nucleic acid hybridisation assays using chemiluminescence quenching. Org. Biomol. Chem. 2009, 7, 386; Browne, K.; Deheyn, D. D.; El-Hiti, G. A.; Smith, K.; Weeks, I. Simultaneous quantification of multiple nucleic acid targets using chemiluminescent probes. J. Am. Chem. Soc. 2011, 133, 14637.
    • 59. Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. 6-Bromotryptamine derivatives from the Gulf of California Tunicate Didemnum Candidum. J. Natl. Prod. 1991, 54, 564.
    • 60. Smith, K.; Lock, S.; El-Hiti, G. A.; Wada, M.; Miyoshi, N. A convenient procedure for bismuth-mediated Barbier-type allylation of aldehydes in water containing fluoride ions. Org. Biomol. Chem. 2004, 2, 935.
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