Synlett 2008(18): 2893-2894  
DOI: 10.1055/s-2008-1067231
© Georg Thieme Verlag Stuttgart ˙ New York

Dimethylboron Bromide (Me2BBr): A Scarcely Recognized Mild and Versatile Reagent with Astonishing Potential

Benoît Y. Michel*
Laboratoire de Synthèse de Biomolécules, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), ­Université Claude Bernard Lyon 1, 69622 Villeurbanne, France
Further Information

Publication History

Publication Date:
15 October 2008 (online)


Originally synthesized by Wiberg et al. [¹] in 1953, dimethylboron bromide was first used in organic synthesis by Guindon. [²] Over the course of the last decades, several applications have been discovered, such as the cleavage of useful protecting groups (MOM, MEM, Me, PMB, Bn, trityl ethers, miscellaneous ketals and acetals), the regio- and stereoselective ring opening of unsymmetrical epoxides, the reductive alkylation of azides, and the deoxygenation of sulfoxides to sulfides. [²b] Some have been reused in total syntheses of complex natural products during the final steps. Thus, its chemoselectivity and its predictable reactivity make it a noteworthy and useful reagent. Nowadays, Me2BBr can be purchased at any chemical supplier. However, this reagent remains expensive; it may be therefore preferable to synthesize it on a preparative scale from BBr3 and SnMe4. [²c] Easily prepared, this colorless pyrophoric liquid (bp 31-32 ˚C) must be stored in solution in dichloromethane. It can be kept for several months under inert atmosphere in the freezer, without any observed decomposition.


  • 1 Wiberg E. Kruerke U. Z. Naturforsch., B.  1953,  8b:  608 
  • 2a Guindon Y. Yoakim C. Morton HE. Tetrahedron Lett.  1983,  24:  2969 
  • 2b Guindon Y. Atkinson JG. Morton HE. J. Org. Chem.  1984,  49:  4538 
  • 2c Guindon Y. Yoakim C. Morton HE. J. Org. Chem.  1984,  49:  3912 
  • 3a Srisiri W. Lamparski HG. O’ Brien DF. J. Org. Chem.  1996,  61:  5911 
  • 3b Rauter AP. Figueiredo J. Ismael M. Canda T. Font J. Figueredo M. Tetrahedron: Asymmetry  2001,  12:  1131 
  • 3c Kodali DR. Duclos RI. Chem. Phys. Lipids  1992,  61:  169 
  • 4a May JA. Namil A. Chen HH. Dantanarayana AP. Dupre B. Liao JC. Bioorg. Med. Chem. Lett.  2006,  14:  2052 
  • 4b Pearson WH. Lee IY. Mi Y. Stoy P. J. Org. Chem.  2004,  69:  9109 
  • 5a Inoue M. Ohashi I. Kawaguchi T. Hirania M. Angew. Chem. Int. Ed.  2008,  47:  1777 
  • 5b Garcia-Fortanet J. Murga J. Carda M. Marco JA. Matesanz R. Diaz JF. Barasoain I. Chem. Eur. J.  2007,  13:  5060 
  • 5c Wender PA. Hilinski MK. Skaanderup PR. Soldermann NG. Mooberry SL. Org. Lett.  2006,  8:  4105 
  • 6a Pattenden G. Ashweek NJ. Baker-Glenn CAG. Kempson J. Walker GM. Yee JGK. Org. Biomol. Chem.  2008,  6:  1478 
  • 6b Mulzer J. Berger M. J. Org. Chem.  2004,  69:  891 
  • 7a Guindon Y. Girard Y. Berthiaume S. Gorys V. Lemieux R. Yoakim C. Can. J. Chem.  1990,  68:  897 
  • 7b Ghosh M. Dulina RG. Kakarla R. Sofia MJ. J. Org. Chem.  2000,  65:  8387 
  • 8 Gridnev ID. Del Rosario MKC. Organometallics  2005,  24:  4519 
  • 9 Michel BY. Krishnakumar KS. Strazewski P. Synlett  2008,  2461 
  • 10 Guindon Y. Ogilvie WW. Bordeleau J. Cui WL. Durkin K. Gorys V. Juteau H. Lemieux R. Liotta D. Simoneau B. Yoakim C. J. Am. Chem. Soc.  2003,  125:  428 
  • 11 Huang H. Drueckhammer DG. Chem. Commun.  2005,  5196 
  • 12 Hoefelmeyer JD. Gabbaï FP. Organometallics  2002,  21:  982