Photocatalytic Synthesis of Glycosyl Bromides

Abstract

Sugar hemiacetals were smoothly transformed into the corresponding glycosyl bromides by treatment with carbon tetrabromide in N,N-dimethylformamide with tris(2,2′-bipyridyl)ruthenium(II) chloride as a catalyst under visible-light irradiation. Protecting groups commonly used in carbohydrate derivatives are unaffected by the mild conditions for bromination.

Key words

carbohydrates - halogenation - bromine - photochemistry - catalysis - ruthenium

• References

• 1a Fujimaki I, Ichikawa Y, Kuzuhara H. Carbohydr. Res. 1982; 101: 148
• 1b Boons G.-J, Isles S, Setälä P. Synlett 1995; 755
• 2 Tropper FD, Andersson FO, Braun S, Roy R. Synthesis 1992; 618
• 3a Tropper FD, Andersson FO, Grand-Maître C, Roy R. Synthesis 1991; 734
• 3b Tsvetkov YE, Byramova NÉ, Backinowsky LV. Carbohydr. Res. 1983; 115: 254
• 4a Roth W, Pigman W. Methods Carbohydr. Chem. 1963; 2: 405
• 4b Spencer RP, Cavallaro CL, Schwartz J. J. Org. Chem. 1999; 64: 3987
• 4c Cavallaro CL, Schwartz J. J. Org. Chem. 1995; 60: 7055
• 4d Hansen T, Daasbjerg K, Skrydstrup T. Tetrahedron Lett. 2000; 41: 8645
• 4e Forbes CL, Franck RW. J. Org. Chem. 1999; 64: 1424
• 4f Zhao J, Wei S, Ma X, Shao H. Carbohydr. Res. 2010; 345: 168
• 5a Matta KL, Girotra RN, Barlow JJ. Carbohydr. Res. 1975; 43: 101
• 5b Fulton DA, Stoddart JF. J. Org. Chem. 2001; 66: 8309
• 5c Ibatullin FM, Shabalin KA, Jänis JV, Shavva AG. Tetrahedron Lett. 2003; 44: 7961
• 5d Xue W, Cheng X, Fan J, Diao H, Wang C, Dong L, Luo Y, Chen J, Zhang J. Tetrahedron Lett. 2007; 48: 6092
• 5e Pei Z, Dong H, Caraballo R, Ramström O. Eur. J. Org. Chem. 2007; 4927
• 6a Koenigs W, Knorr E. Ber. Dtsch. Chem. Ges. 1901; 34: 957
• 6b Lipták A, Nánási P, Neszmélyi A, Wagner H. Tetrahedron 1980; 36: 1261
• 6c Presser A, Kunert O, Pötschger I. Monatsh. Chem. 2006; 137: 365
• 6d Beale TM, Taylor MS. Org. Lett. 2013; 15: 1358
• 7a Ditmar R. Monatsh. Chem. 1902; 23: 865
• 7b Fischer E, Fischer H. Ber. Dtsch. Chem. Ges. 1910; 43: 2521
• 7c Fischer E. Ber. Dtsch. Chem. Ges. 1911; 44: 1898
• 7d Koto S, Morishima N, Irisawa T, Hashimoto Y, Yamazaki M, Zen S. Nippon Kakgaku Kaishi 1982; 1651
• 7e Koto S, Morishima N, Shichi S, Haigoh H, Hirooka M, Okamoto M, Higuchi T, Shimizu K, Hashimoto Y, Iriawa T, Kawasaki H, Takahashi Y, Yamazaki M, Mori Y, Kudo K, Ikegaki T, Suzuki S, Zen S. Bull. Chem. Soc. Jpn. 1992; 65: 3257
• 7f Kartha CP. R, Jennings HJ. J. Carbohydr. Chem. 1990; 9: 777
• 7g Larsen K, Olsen CE, Motawia MS. Carbohydr. Res. 2003; 338: 199
• 8a Montero J.-L, Winum J.-Y, Leydet A, Kamal M, Pavia AA, Roque J.-P. Carbohydr. Res. 1997; 297: 175
• 8b Schmidt RR, Rilcker E. Tetrahedron Lett. 1980; 21: 1421
• 9 Gillard JW, Israel M. Tetrahedron Lett. 1981; 22: 513
• 10a Hanessian S, Ponpipom MM. Lavallee P. 1972; 24: 45
• 10b Pinto BM, Reimer KB, Morissette DG, Bundle DR. J. Org. Chem. 1989; 54: 2650
• 10c Iversen T, Bundle DR. Carbohydr. Res. 1982; 103: 29
• 11 Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
• 12a Andrews RS, Becker JJ, Gagné MR. Angew. Chem. Int. Ed. 2010; 49: 7272
• 12b Wever WJ, Cinelli MA, Bowers AA. Org. Lett. 2013; 15: 30
• 12c Spell M, Wang X, Wahba AE, Conner E, Ragains J. Carbohydr. Res. 2013; 369: 42
• 13 Dai C, Narayananam JM. R, Stephenson CR. J. Nat. Chem. 2011; 3: 140
• 14 Bhowmik S, Maitra U. Chem. Commun. 2012; 48: 4624
• 15 Richards S.-J, Jones MW, Hunaban M, Haddleton DM, Gibson MI. Angew. Chem. Int. Ed. 2012; 51: 7812
• 16 Braitsch M, Kählig H, Kontaxis G, Fischer M, Kawada T, Konrat R, Schmid W. Beilstein J. Org. Chem. 2012; 8: 448
• 17 Zhang Z, Magnusson G. Carbohydr. Res. 1996; 295: 41
• 18 Zheng X, Morgan J, Pandey SK, Chen Y, Tracy E, Baumann H, Missert JR, Batt C, Jackson J, Bellnier DA, Henderson BW, Pandey RK. J. Med. Chem. 2009; 52: 4306