Easy Access to α-Bromoketones and Epoxides from vic-Dibromides Under Aqueous Conditions

REFERENCES

• (a) Li , C. J. ; Chang , T. H. In Organic Reactions in Aqueous Media ; Wiley : New York , 1997 ; (b) Grieco , P. A. Organic Synthesis in Water ; Blackie Academic and Professional : London , 1998 .
   Google Scholar
• Lindström , U. M. Organic Reactions in Water: Principles, Strategies, and Applications ; Blackwell : Oxford , 2007 .
   Google Scholar
• (a) Azizi , N. ; Saidi , M. R. Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water . Org. Lett. 2005 , 7 , 3649 – 3651 ; (b) Azizi , N. ; Aryanasab , F. ; Torkiyan , L. ; Ziyaei , A. ; Saidi , M. R. One-pot synthesis of dithiocarbamates accelerated in water . J. Org. Chem. 2006 , 71 , 3634 – 3635 ; (c) Khatik , G. L. ; Kumar , R. ; Chakraborti , A. K. Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water . Org. Lett. 2006 , 8 , 2433 – 2436 .
   PubMed Web of Science ®Google Scholar
• (a) Stamatov , S. D. ; Stawinski , J. Regioselective and tereospecific halosilylating cleavage of the oxirane system of glycidol derivatives as an efficient strategy to C2-O-functionalized C3-vicinal halohydrins . Eur. J. Org. Chem. 2008 , 2635 – 2643 ; (b) Moriuchi , T. ; Yamaguchi , M. ; Kikushima , K. ; Hirao , T. An efficient vanadium-catalyzed bromination reaction . Tetrahedron Lett. 2007 , 48 , 2667 – 2670 ; (c) Urankar , D. ; Rutar , I. ; Modec , B. ; Dolenc , D. Synthesis of bromo- and iodohydrins from deactivated alkenes by use of N-bromo- and N-iodosaccharin . Eur. J. Org. Chem. 2005 , 2349 – 2353 ; (d) Dagani , M. J. ; Barda , H. J. ; Benya , T. J. ; Sanders , D. C. Ullmann's Encyclopedia of Industrial Chemistry: Bromine Compounds; Wiley-WCH Verlag GmbH & Co.: Weinheim, 2002; (e) Larock , R. C. Comprehensive Organic Transformations, 2nd ed.; VCH: New York, 1999; pp 715–719; (f) Bryan , L. ; Charles , K F. ; Chiu , R. F. ; Hank , J. M. ; Joshua , R.; Harry, T. An optimized process for formation of 2,4-disubstituted imidazoles from condensation of amidines and α-Haloketones . Org. Process Res.Dev. 2002 , 6 , 682 – 683 ; (g) Takayuki , T. ; Saeko , I. ; Hiroshi , S. ; Koichiro , O. TiCl4–n-Bu4NI as a reducing reagent: Pinacol coupling and enolate formation from α-haloketones . J. Org. Chem. 2000 , 65 , 5066 – 5068 ; (h) Bartlett , P. A. In Asymmetric Synthesis; Academic Press: New York, 1984; (i) Erickson , R. E. In Marine Natural Products; Academic Press: New York, 1986.
   Google Scholar
• (a) Majetich , G. ; Hicks , R. ; Reister , S. Electrophilic aromatic bromination using bromodimethylsulfonium bromide generated in situ. J. Org. Chem. 1997, 62, 4321–4326; (b) Bonini , C. ; Righi , G. Regio- and chemoselective synthesis of halohydrins by cleavage of oxiranes with metal halides. Synthesis 1994, 225–238; (c) Smith , J. G. ; Fieser , M. Fieser and Fieser's Reagent for Organic Synthesis; John Wiley and Sons: New York, 1990; vols. 1–12; (d) Reddy , M. A. ; Surendra , K. ; Bhanumathi , N. ; Rama Rao , K. Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin. Tetrahedron 2002, 58, 6003–6008; (e) Sharghi , H. ; Niknam , K. ; Pooyan , M. The halogen-mediated opening of epoxides in the presence of pyridine-containing macrocycles. Tetrahedron 2001, 57, 6057–6064; (f) Ranu , B. C. ; Banerjee , S. Ionic liquid as reagent: A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions. J. Org. Chem. 2005, 70, 4517–4519; (g) Shimizu , M. ; Yoshida , A. ; Fujisawa , T. Regioselective conversion of epoxides to halohydrins by titanium(IV) halide–lithium halide complex. Synlett 1992, 204–206; (h) Ciaccio , J. A. ; Heller , E. ; Talbot , A. Regio- and chemoselective ring opening of epoxides to bromohydrins with dilithium tetrabromocuprate. Synlett 1991, 248–250.
   PubMed Web of Science ®Google Scholar
• (a) Damin , B. ; Garapon , J. ; Silion , B. A convenient synthesis of chlorohydrins using chloramine T . Synthesis 1981 , 362 – 363 ; (b) Rolston , J. H. ; Yates , K. Polar additions to the styrene and 2-butene systems, I: Distribution stereochemistry of bromination products in acetic acid . Am. Chem. Soc. 1969 , 91 , 1469 – 1476 ; (c) Dalton , D. R. ; Dutta , V. P. ; Jones , D. C. Bromohydrin formation in dimethyl sulfoxide . J. Am. Chem. Soc. 1968 , 90 , 5498 – 5501 ; (d) Chamberlin , A. R. ; Dezube , M. ; Dussalt , P. ; McMills , M. C. Iodocyclization of allylic alcohol derivatives containing internal nucleophiles: Control of stereoselectivity by substituents in the acyclic precursors . J. Am. Chem. Soc. 1983 , 105 , 5819 – 5825 ; (e) Barluenga , J. ; Marco-Arias , M. ; Gonzalez-Bobes , F. ; Ballesteros , A. ; Gonzalez , J. M. Reaction of akenes with hydrogen peroxide and sodium iodide: A nonenzymatic biogenic-like approach to iodohydrins . Chem. Eur. J. 2004 , 10 , 1677 – 1682 ; (f) Masuda , H. ; Takase , K. ; Nishio , M. ; Hasegawa , A. ; Nishiyam , Y. ; Ishii , Y. A new synthetic method of preparing iodohydrin and bromohydrin derivatives through in situ generation of hypohalous acids from H5IO6 and NaBrO3 in the presence of NaHSO3 . J. Org. Chem. 1994 , 59 , 5550 – 5555 ; (g) Yadav , J. S. ; Reddy , B. V. S. ; Baishya , G. ; Harshavardhan , S. J. Green approach for the conversion of olefins into vic-halohydrins using N-halosuccinimides in ionic liquids . Tetrahedron Lett. 2005 , 46 , 3569 – 3572 ; (h) Hanzlik , R. P. Organic Syntheses; Wiley & Sons: New York, 1988; vol. 6, pp. 560–564; (i) Vishwakarma , L. C. ; Walia , J. S. A convenient and exclusive methoxybromiation of alkenes . J. Ind. Chem. Soc. 1976 , 53 , 156 – 162 .
   Google Scholar
• (a) Garbisch , Jr. E. W. Cycloalk-2-enones and α,β,α′,β′-cycloalkadienones, A: Synthesis, B: On the direction of bromination of 2-substituted cycloalkanones and their ketals . J. Org. Chem. 1965 , 30 , 2109 – 2120 ; (b) Diwu , Z. ; Beachdel , C. ; Klaubert , D. H. A facile protocol for the convenient preparation of amino-substituted α-bromo- and α,α-dibromo arylmethylketones . Tetrahedron Lett. 1998 , 39 , 4987 – 4990 ; (c) Patai , S. ; Rappoport , Z. The Chemistry of Functional Groups: Supplement D2, the Chemistry of Halides, Pseudo-Halides and Azides, Parts 1 and 2; Wiley: Chichester, 1995; (d) Attanasi , O. A. ; Berretta , S. ; Favi , G. ; Filippone , G. P. ; Mele , G. ; Moscatelli , G. ; Saladino , R. Tetrabromo hydrogenated cardanol: Efficient and renewable brominating agent . Org. Lett. 2006 , 8 , 4291 – 4293 ; (e) Choi , H. Y. ; Chi , D. Y. Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon . Org. Lett. 2003 , 5 , 411 – 414 ; (f) Paul , S. ; Gupta , V. ; Gupta , R. A simple and selective procedure for α-bromination of alkanones using hexamethylenetetramine–bromine complex and basic alumina in solvent-free conditions . Synth. Commun. 2003 , 33 , 1917 – 1922 ; (g) Goswami , J. ; Goswami , A. Selective bromination of acetophenone derivatives with bromine in methanol . J. Indian Chem. Soc. 2002 , 79 , 469 – 471 ; (h) Ghiaci , M. ; Asghari , J. Increasing the selectivity of bromination of aromatic compounds using Br2/SiO2 . Bull. Chem. Soc. Jpn. 2001 , 74 , 1151 – 1152 ; (i) Sket , B. ; Zupan , M. α-Bromination of ketones with the bromine omplex of poly(styrene-co-4-vinylpyridine) . Synth. Commun. 1989 , 19 , 2481 – 2487 .
   Web of Science ®Google Scholar
• (a) Guha , S. K. ; Wu , B. ; Kim , B. S. ; Baik , W. ; Koo , S. TMS·OTf-catalyzed α-bromination of carbonyl compounds by N-bromosuccinimide. Tetrahedron Lett. 2006, 47, 291–293; (b) Meshram , H. M. ; Reddy , P. N. ; Vishnu , P. ; Sadashiv , K. ; Yadav , J. S. A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids. Tetrahedron Lett. 2006, 47, 991–995; (c) Pravst , I. ; Zupan , M. ; Stavber , S. Directed regioselectivity of bromination of ketones with NBS: Solvent-free conditions versus water. Tetrahedron Lett. 2006, 47, 4707–4710; (d) Pravst , I. ; Zupan , M. ; Stavber , S. Solvent-free bromination of 1,3-diketones and β-keto esters with NBS. Green Chem. 2006, 8, 1001–1005; (e) Das , B. ; Venkateswarlu , K. ; Mahender , G. ; Mahender , I. A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst. Tetrahedron Lett. 2005, 46, 3041–3044; (f) Tanemura , K. ; Suzuki , T. ; Nishida , Y. ; Satsumabayashi , K. ; Horaguchi , T. A mild and efficient procedure for alpha-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate. Chem. Commun. 2004, 470–471; (g) Yang , D. ; Yan , Y. L. ; Lui , B. Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids. J. Org. Chem. 2002, 67, 7429–7431.
   Google Scholar
• Bertelsen , S. ; Halland , N. ; Bachmann , S. ; Marigo , M. ; Braunton , A. ; Jørgensen , K. A. Organocatalytic asymmetric α-bromination of aldehydes and ketones . Chem. Commun. 2005 , 4821 – 4823 .
   PubMedGoogle Scholar
• (a) Adimurthy , S. ; Ramachandraiah , G. ; Bedekar , A. V. ; Ghosh , S. ; Ranu , B. C. ; Ghosh , P. K. Eco-friendly and versatile brominating reagent prepared from liquid bromine precursor . Green Chem. 2006 , 8 , 916 – 921 ; (b) Adimurthy , S. ; Ghosh , S. ; Patoliya , P. U. ; Ramachandraiah , G. ; Agrawal , M. K. ; Gandhi , M. R. ; Upadhyay , S. C. ; Ghosh , P. K. ; Ranu , B. C. An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives, and ketones using a bromide/bromate couple . Green Chem. 2008 , 10 , 232 – 237 ; (c) Adimurthy , S. ; Ramachandraiah , G. ; Ghosh , P. K. assemblies as promoters of iodohydrin formation . Synth. Commun. 2007 , 37 , 1579 – 1585 ; (d) Agrawal , M. K. ; Adimurthy , S. ; Ganguly , B. ; Ghosh , P. K. Comparative study of the vicinal functionalization of olefins with 2:1 bromide–bromate and iodide–iodate reagents . Tetrahedron 2009 , 65 , 2791 – 2797 ; (e) Patil , R. D. ; Joshi , G. ; Adimurthy , S. ; Ranu , B. C. Facile and one-pot synthesis of α-bromoketones from olefins with an alternative brominating agent . Tetrahedron Lett. 2009 , 50 , 2529 – 2532 .
   Web of Science ®Google Scholar
• Tang , J. ; Zhu , J. ; Shen , Z. ; Zhang , Y. Efficient and convenient oxidation of organic halides to carbonyl compounds by H2O2 in ethanol . Tetrahedron Lett. 2007 , 48 , 1919 – 1921 .
   Web of Science ®Google Scholar