Bromination of Enamines from Tertiary Amides Using the Petasis Reagent: A Convenient One-Pot Regioselective Route to Bromomethyl Ketones

REFERENCES

• De Kimpe , N. ; Verhé , R. The Chemistry of α-Haloketones, α-Haloaldehydes, and α-Haloimines ; S. Patai , Z. Rappoport (Eds.); John Wiley and Sons : Chichester , 1988 , pp. 1 – 119 .
   Google Scholar
• (a) Gaudry , M. ; Marquet , A. Enolisation des cétones dissymétriques-III: Accès facile aux bromométhylcétones par bromation en présence de méthanol . Tetrahedron 1970 , 26 , 5611 – 5617 ; (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 ( 28 ), 4987 – 4990 .
   Google Scholar
• (a) King , L. C. ; Ostrum , G. K. J. Selective brominination with copper(II) bromide . J. Org. Chem. 1964 , 29 , 3459 – 3461 ; (b) El-Qisairi , A. ; Qaseer , H. A. Bromination of ketones by palladium(II): An asymmetric synthesis of α-bromoketones . Jordan J. Chem. 2007 , 2 , 69 – 78 .
   Web of Science ®Google Scholar
• (a) Lee , J. C. ; Bae , Y. H. ; Chang , S.-K. Efficient α-halogenation of carbonyl compounds by N-bromosuccinimide and N-chlorosuccinimde. Bull. Korean Chem. Soc. 2003, 24(4), 407–408; (b) Jagdale , A. R. ; Chouthaiwale , P. V. ; Sudalai , A. Cu(Otf)2-catalyzed α-halogenation of ketones with 1,3-dichloro-5,5′-dimethylhydantoin and N-bromosuccinimide. Indian J. Chem. 2009, 48B, 1424–1430; (c) El-Khazzouli , S. ; Berteina-Raboin , S. ; Mouaddib , A. ; Guillaumet , G. Solid-support synthesis of 2,4-disubstituted thiazoles and aminothiazoles. Tetrahedron Lett. 2002, 43, 3193–3196; (d) Pravst , I. ; Zupan , M. ; Stavber , S. Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions. Tetrahedron 2008, 64, 5191–5199; (e) Arbuj , S. S. , Waghmode , S. B. ; Ramaswamy , A. V. Photochemical α-bromination of ketones using N-bromosuccinimide: A simple, mild, and efficient method. Tetrahedron Lett. 2007, 48, 1411–1415.
   Web of Science ®Google Scholar
• Kajigaeshi , S. ; Kakinami , T. ; Okamoto , T. ; Fujisaki , S. Synthesis of bromoacetyl derivatives by use of tetrabutylammonium tribromide . Bull. Chem. Soc. Jpn. 1987 , 60 , 1159 – 1160 .
   Web of Science ®Google Scholar
• Habermann , J. ; Ley , S. V. ; Smits , R. Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents . J. Chem. Soc., Perkin Trans. 1 1999 , 17 , 2421 – 2423 .
   Google Scholar
• Borikar , S. P. ; Daniel , T. Aromatic bromination of aldehydes and ketones using 1,3-di-n-butylimidazolium tribromide [BBIm]Br3 ionic liquids under solvent-free conditions . J. Iran. Chem. Soc. 2011 , 8 ( 2 ), 531 – 536 .
   Web of Science ®Google Scholar
• Patil , R. D. ; Joshi , G. ; Adimurthy , S. ; Ranu , B. C. Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent . Tetrahedron Lett. 2009 , 50 , 2529 – 2532 .
   Web of Science ®Google Scholar
• Lee , J. C. ; Park , J. Y. ; Yoon , S. Y. ; Bae , Y. H. ; Lee , S. J. Efficient microwave-induced direct α-halogenation of carbonyl compounds . Tetrahedron Lett. 2004 , 45 , 191 – 193 .
   Web of Science ®Google Scholar
• Ostapiuk , Y. V. ; Matiichuk , V. S. ; Pidlypnyi , N. I. ; Obushak , N. D. Convenient synthesis of α-bromo ketones by the Meerwein reaction . Russian J. Org. Chem. 2012 , 48 ( 4 ), 519 – 522 .
   Web of Science ®Google Scholar
• Podgorsek , A. ; Stavber , S. ; Zupan , M. ; Iskra , J. Bromination of ketones with H2O2-HBr “on water” . Green Chem. 2007 , 9 , 1212 – 1218 .
   Web of Science ®Google Scholar
• Izumisawa , Y. ; Togo , H. Preparation of α-bromoketones and thiazoles from ketones with NBS and thioamides in ionic liquids . Green Sustainable Chem. 2011 , 1 , 54 – 62 .
   Google Scholar
• (a) Catch , J. R. ; Elliot , D. F. ; Hay , D. H. ; Jones , E. R. H. Halogenated ketones, part III: The preparation of bromomethyl ketones by the diazomethane reaction . J. Chem. Soc. 1948 , 278a ; (b) Shi , H. ; Uttamchandani , M. ; Yao , S. Q. Applying small molecule microarrays and resulting affinity probe cocktails for proteome profiling of mammalian cell lysates . Chem. Asian J. 2011 , 6 , 2803 – 2815 ; (c) Shi , H. ; Liu , K. ; Xu , A. ; Yao , S. Q. Small molecule microarray (SMM)–facilitated screening of affinity-based probes (AfBPs) for γ-secretase . Chem. Commun. 2009 , 5030 – 5032 .
   Google Scholar
• Keana , J. F. W. ; Schumaker , R. R. A new method for the selective halogenation of the methyl group of methyl ketones . Tetrahedron 1970 , 26 , 5191 – 5194 .
   Web of Science ®Google Scholar
• Calo , V. ; Lopez , L. ; Valentino , D. S. Direct regiospecific synthesis of bromoketones from epoxides . Synthesis 1978 , 2 , 139 – 140 .
   Google Scholar
• Taguchi , H. ; Yamamoto , H. ; Nozaki , H. A simple synthesis of α-haloketones via β-oxido carbenoids . Tetrahedron Lett. 1972 , 14 , 4661 – 4662 .
   Google Scholar
• (a) Blanco , L. ; Amice , P. ; Conia , J. M. Halogenation of enol silyl ethers: Synthesis of various types of α-bromocarbonyl compounds . Synthesis 1976 , 3 , 194 – 195 .
   Google Scholar
• Cook , A. G. (Ed.). Enamines: Synthesis, Structure and Reactions ; Decker : New York , 1969 .
   Google Scholar
• Herdeis , C. ; Heller , E. Synthesis of 2S,5S and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene . Tetrahedron: Asymmetry 1993 , 4 , 2085 – 2094 .
   Web of Science ®Google Scholar
• Tehrani , A. ; De Kimpe , N. New synthesis of 2-methyleneaziridines and 2-methyleneazetidines by dimethyl titanocene–mediated methylation of α- and β-lactams . Tetrahedron Lett. 2000 , 41 , 1975 – 1978 .
   Web of Science ®Google Scholar
• Martinez , I. ; Howell , A. R. The reaction of dimethyltitanocene with N-substituted-β-lactams. Tetrahedron Lett. 2000, 41, 5607–5611.
   Web of Science ®Google Scholar
• Petasis , N. A. , Bzowej , E. I. Titanium-mediated carbonyl olefinations: Methylenations of carbonyl compounds with dimethyltitanocene . J. Am. Chem. Soc. 1990 , 112 ( 17 ), 6392 – 6394 .
   Web of Science ®Google Scholar
• Payack , J. F. ; Hughes , D. L. ; Cai , D. ; Cottrell , I. F. ; Verhoeven , T. R. Dimethyltitanocene . Org. Synth. 2002 , 79 , 19 .
   Google Scholar
• Petasis , N. A. ; Lu , S. P. Methylenations of heteroatom-substituted carbonyls with dimethyl titanocene . Tetrahedron Lett. 1995 , 36 , 2393 – 2396 .
   Web of Science ®Google Scholar
• Rappe , C. ; Carlson , R. Bromination of enamines from methyl isopropyl ketone: A possible route to bromomethyl isopropyl ketone . Acta Chim. Scand. B 1974 , 28 , 1060 – 1064 .
   Google Scholar
• Carlson , R. Bromination of enamines from methyl isopropyl ketone: Bromination of 2-(1-pyrrolidinyl)-3-methyl-1-butene . Acta Chim. Scand. B 1980 , 34 , 157 – 160 .
   Google Scholar
• Carlson , R. Halogenation of enamines: Regioselective synthesis of halomethyl ketones . Acta Chim. Scand. B 1978 , 32 , 646 – 650 .
   Google Scholar