KHSO₄-Catalyzed Synthesis of 1,1′-Oxybis(2-bromoethane-1,1-diyl)dibenzenes and 1-(1-(Benzyloxy)-2-bromoethyl)benzenes Under Solvent-Free Conditions

REFERENCES

• (a) Anastas , P. T. ; Warner , J. C. Green Chemistry: Theory and Practice ; Oxford University Press : Oxford , 1998 ; (b) Winterton , N. Twelve more green chemistry principles. Green Chem. 2001, 3, G73–G75; (b) Horváth , I. T. Innovations and green chemistry. Chem. Rev. 2007, 107, 2169–2173; (c) Sheldon , R. A. E factors, green chemistry, and catalysis: An odyssey. Chem. Commun. 2008, 3352–3365; (d) Anastas , P. T. ; Zimmermann , J. B. Peer reviewed: Design through the 12 principles of green engineering. Environ. Sci. Technol. 2003, 37, 94A–101A; (e) Tang , S. L. Y. ; Smith , R. L. S. ; Poliakoff , M. Principles of green chemistry: Productively. Green Chem. 2005, 7, 761–762.
   Google Scholar
• (a) Tanaka , K. ; Toda , F. Solvent-free organic synthesis . Chem. Rev. 2000 , 100 , 1025 – 1074 ; (b) Rothenberg , G. ; Downie , A. P. ; Raston , C. L. ; Scott , J. L. Understanding solid/solid organic reactions . J. Am. Chem. Soc. 2001 , 123 , 8701 – 8708 ; (c) Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
   PubMed Web of Science ®Google Scholar
• (a) Sugahara , T. ; Fukuda , H. ; Iwabuchi , Y. Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1β converting enzyme inhibitor . J. Org. Chem. 2004 , 69 , 1744 – 1747 ; (b) Trost , B. M. ; Tang , W. An enantioselective strategy to macrocyclic bisindolylmaleimides: An efficient formal synthesis of LY 333531 . Org. Lett. 2001 , 3 ( 21 ), 3409 – 3411 ; (c) Kohll , M. J. ; Lejeune , R. G. Coupling of biologically active steroids to conjugating arms through ether linkages for use in immunochemistry. Steroids 2002 67 , 71 – 75 ; (d) Izuhara , T. ; Katoh , T. Studies toward the total synthesis of scyphostatin: First entry to the highly functionalized cyclohexenone segment . Org. Lett. 2001 , 3 , 1653 – 1656 ; (e) Adhikari , S. ; Roy , S. C. Stereoselective radical annulation route to the synthesis of (±)-paulownin and (±)-isogmelinol . Tetrahedron Lett. 1992 , 33 , 6025 – 6026 ; (f) Maiti , G. ; Adhikari , S. ; Roy , S. C. Stereoselective total synthesis of (±)-samin and the dimethoxy analogue, the general furofuran lignan precursors . Tetrahedron 1995 , 51 , 8389 – 8396 .
   PubMed Web of Science ®Google Scholar
• (a) Jasti , R. ; Vitale , J. ; Rychnovsky , S. D. Axial-selective prins cyclizations by solvolysis of α -bromo ethers . J. Am. Chem. Soc. 2004 , 126 , 9904 – 9905 ; (b) Guindon , Y. ; Ogilvie , W. W. ; Bordeleau , J. ; Cui , W. L. ; Durkin , K. ; Gorys , V. ; Juteau , H. ; Lemieux , M. ; Liotta , D. ; Simoneau , B. ; Yoakim , C. Axial-selective prins cyclizations by solvolysis of α-bromo ethers . J. Am. Chem. Soc. 2003 , 125 , 428 – 436 ; (c) Van-Orden , L. J. Patterson , B. D. ; Rychnovsky , S. D. Total synthesis of leucascandrolide A: A new application of the mukaiyama aldol−prins reaction . J. Org. Chem. 2007 , 72 , 5784 – 5793
   PubMed Web of Science ®Google Scholar
• (a) Esteves , A. P. ; Ferreira , E. C. ; Medeiros , M. J. Selective radical cyclisation of propargyl bromoethers to tetrahydrofuran derivatives via electrogenerated nickel(I) tetramethylcyclam . Tetrahedron 2007 , 63 , 3006 – 3009 ; (b) Dunach , E. ; Esteves , A. P. ; Medeiros , M. J. ; Oliverob , S. Electrochemical intramolecular cyclisation of propargyl bromoethers catalysed by nickel complexes . New J. Chem. 2005 , 29 , 633 – 636 .
   Web of Science ®Google Scholar
• Montorne , J. M. ; Reina , J. A. ; Ronda , J. C. Studies on the modification of poly(ω-bromoalkyl-1-glycidylether)s with 4′-methoxybiphenyl-4-oxy mesogenic groups . J. Poly. Sci. Part A: Poly. Chem. 2005 , 43 , 5998 – 6006 .
   Web of Science ®Google Scholar
• (a) Yu , W. ; Jin , Z. A highly stereoselective synthesis of α -halo vinyl ethers and their applications in organic synthesis. J. Am. Chem. Soc. 2000, 122, 9840–9841; (b) Tanuwidjaja , J. ; Ng , S. S. ; Jamison , T. F. Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade. J. Am. Chem. Soc. 2009, 131, 12084–12085.
   Web of Science ®Google Scholar
• (a) Suzuki , T. ; Suzuki , M. Diversity of halogenated secondary metabolites in the red alga Laurencia Nipponica (rhodamelaceae, ceramiale) . J. Phycol. 1997 , 33 , 196 – 208 ; (b) Brito , I. ; Dias , T. ; Dıaz-Marrero , A. R. ; Darias , J. ; Cueto , M. Aplysiadiol from Aplysia dactylomela suggested a key intermediate for a unified biogenesis of regular and irregular marine algal bisabolene-type metabolites . Tetrahedron 2006 , 62 , 9655 – 9660 .
   Web of Science ®Google Scholar
• Swallen , L. C. ; Boor , C. E. The synthesis of β-bromo-alkyl ethers and their use in further synthesis . J. Am. Chem. Soc. 1930 , 52 , 651 – 660 .
   Google Scholar
• Skumov , M. Y. ; Brailovskii , S. M. ; Temkin , O. N. New approaches to syntheses of diethers and haloethers from cyclopentadiene . Russ. Chem. Bull., Int. Ed. 2002 , 51 , 616 – 624 .
   Web of Science ®Google Scholar
• (a) Zolotarev , R. N. ; Yakovlev , M. E. ; Razin , V. V. Synthesis of 3-oxatricyclo[4.4.0.02,7]decene derivatives . Russ, J. Org. Chem. 2006 , 42 , 1636 – 1642 ; (b) Cwynar , V. ; Donahue , M. G.; Hart D. J. ; Yang , D. Quassinoid support studies: Fused carbocycle synthesis from benzoic acid derivatives via 5-hexynyl and 6-heptynyl radical cyclizations . Org. Lett. 2006 , 8 , 4577 – 4580 .
   Web of Science ®Google Scholar
• Phukan , P. ; Chakraborty , P. ; Kataki , D. A simple and efficient method for regioselective and stereoselective synthesis of vicinal bromohydrins and alkoxybromides from an olefin . J. Org. Chem. 2006 , 71 , 7533 – 7537
   PubMed Web of Science ®Google Scholar
• James , M. P. Process for preparing bis-bromoalkyl ethers. U.S. Patent 4629814, 1986 .
   Google Scholar
• Hajra , S. ; Karmakar , A. ; Bhowmick , M. Silver(I)-promoted asymmetric halomethoxylation of chiral α,β-unsaturated carboxylic acid derivatives: Enantioselective synthesis of N-protected syn-β-methoxy-α -amino acids . Tetrahedron: Asymmetry 2006 , 17 , 210 – 222 .
   Web of Science ®Google Scholar
• Zhang , Z.-H. ; Li , T.-S. Applications of zirconium(IV) compounds in organic synthesis . Curr. Org. Chem. 2009 , 13 , 1 – 30 .
   Web of Science ®Google Scholar
• Adimurthy , S. ; Ramachandraiah , G. Reductive dehalogenation of halophenols in sulfite–bisulfate medium . Tetrahedron Lett. 2004 , 45 , 5251 – 5252 .
   Web of Science ®Google Scholar
• Patil , R. D. ; Joshi , G. ; Adimurthy , S. KHSO4: A highly efficient and reusable heterogeneous catalyst for hydroarylation of styrenes . Monatsh Chem. 2010 , 141 , 1093 – 1099
   Web of Science ®Google Scholar
• (a) Ayta , W. E. F. ; Dantas , N. O. ; Silva , A. C. A. ; Cano , N. F. First evidence of crystalline KHSO4:Mn grown by an aqueous solution method and the investigation of the effect of ionizing radiation exposure . J. Cryst. Growth 2010 , 312 , 563 – 567 ; (b) Knudsen , C. B. ; Kalampounias , A. G. ; Fehrmann , R. ; Boghosian , S. Thermal dissociation of molten KHSO4: Temperature dependence of Raman spectra and thermodynamics . J. Phys. Chem. B 2008 , 112 , 11996 – 12000 ; (c) Gowsami , A. ; Das , R. N. ; Borthakur , N. KHSO4-SiO2-MeOH: An efficient selective solid-supported system for deprotection of alcohols from esters . Indian J. Chem. 2007 , 46B , 1893 – 1895 ; (e) Bita , B. ; Majid , M. H. ; Hossein , A. O. Practical and efficient synthesis of 3-aryl-2H-benzo[1,4]thiazine derivatives catalyzed by KHSO4 . Synth. Commun. 2011 , 41 , 589 – 593 .
   Web of Science ®Google 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 a liquid bromine precursor. Green Chem. 2006, 8, 916–922; (b) Adimurthy , S. ; Ghosh , S. ; Patoliya , P. U. ; Ramachandraiah , G. ; Agrawal , M. ; 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) 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; (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) Joshi , G. ; Bhadra , S. ; Ghosh , S. ; Agrawal , M. K. ; Ganguly , B. ; Adimurthy , S. ; Ghosh , P. K. ; Ranu , B. C. Making full use of the oxidizing equivalents in nromate in the selective oxidation of thiols, sulfides and benzylic/secondary alcohols in to disulfides, sulfoxides, and aldehydes/ketones. Ind. Eng. Chem. Res. 2010, 49, 1236–1241; (f) Patil , R. D. ; Joshi , G. ; Adimurthy , S. HBr-H2O2: A facile protocol for the regioselective synthesis of bromohydrins and α -bromoketones and oxidation of benzylic/secondary alcohols to carbonyl compounds under very mild aqueous conditions. Ind. Eng. Chem. Res. 2010, 49, 8100–8105.
   Web of Science ®Google Scholar
• (a) Jolles , Z. E. ; Oxtoby , A. H. ; Radford , P. J. M. Bromine and Its Compounds ; Ernest Benn. Limited : London , 1966 ; p. 527 ; (b) Jan , B. M. G. ; Alexander , D. E. Process for the preparation of omega-bromostyrene and 4-methyl-omega-bromostyrene, U.S. Patent 2,824,144, 1958 .
   Google Scholar