Synthesis of vinyl bromides

Recent Literature

Organotrifluoroborates are rapidly and regioselectively converted into organic bromides in excellent yields under mild conditions, using sodium bromide in the presence of chloramine-T.
G. W. Kabalka, A. R. Mereddy, Organometallics, 2004, 23, 4519-4521.

Application of (PhO)₃P-halogen-based reagents allows the preparation of vinyl halides in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.
A. Spaggiari, D. Vaccari, P. Davoli, G. Torre, F. Prati, J. Org. Chem., 2007, 72, 2216-2219.

(E)-β-Arylvinyl bromides were readily prepared in a short reaction time (1-2 min) by microwave irradiation of the corresponding 3-arylpropenoic acids in the presence of N-bromosuccinimide and a catalytic amount of lithium acetate.
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Synthesis, 2005, 1319-1325.

Using triethylamine as catalyst in Hunsdiecker reactions with N-halosuccinimides as Br⁺ or I⁺ source, cinnamic acids, and propiolic acids are converted to the corresponding α-halostyrenes and 1-halo-1-alkynes in good isolated yields within 1-5 min.
J. Prakash, S. Roy, J. Org. Chem., 2002, 67, 7861-7864.

Oxidative bromination of different types of olefins using Selectfluor/KBr afforded addition, monobromo-substituted, or Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem., 2004, 69, 8561-8563.

C. Ye, J. M. Shreeve, J. Org. Chem., 2004, 69, 8561-8563.

Use of a zirconocene catalyst based on the Brintzinger ligand and catalytic amounts of methyl aluminoxanes (MAO) effect a >99% regiocontrol of Negishi carboaluminations of 1-alkynes in toluene.
B. H. Lipshutz, T. Butler, A. Lower, J. Am. Chem. Soc., 2006, 128, 15396-15398.

Unsaturated compounds such as alkenes, alkynes, allenes, and methylenecyclopropanes (MCPs) can be dibrominated within minutes by NBS and lithium bromide in THF at room temperature in good to excellent yields under mild conditions.
L.-X. Shao, M. Shi, Synlett, 2006, 1269-1271.

L.-X. Shao, M. Shi, Synlett, 2006, 1269-1271.

α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared in good yields by addition of hydrobromic acid or hydrochloric acid to α,β-unsaturated carbonyl compounds in the presence of Oxone in CH₂Cl₂ followed by treatment of the resulting dihalides with Et₃N.
K.-M. Kim, I.-H. Park, Synthesis, 2004, 2641-2644.

A stereoselective multicomponent synthesis of (Z)-β-bromo Baylis-Hillman ketones uses MgBr₂ as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity.
H.-X. Wei, R. L. Jasoni, J. Hu, G. Li, P. W. Pare, Tetrahedron, 2004, 60, 10233-10237.

A convenient and efficient method for aminobromination of alkylidenecyclopropanes is reported. This is exemplified in the stereoselective preparation of N-[(Z)-3-bromobut-3-en-1-yl]-p-toluenesulfonamides by using p-toluenesulfonamide and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively.
X. Huang, W.-J. Fu, Synthesis, 2006, 1016-1017.

Poly{[4-(hydroxy)(tosyloxy)iodo]styrene} was efficient in the halotosyloxylation reaction of alkynes with iodine or NBS or NCS. The polymer reagent could be regenerated and reused.
J.-M. Chen, X. Huang, Synthesis, 2004, 1557-1558.

Related:

An optimized Julia olefination between readily available α-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities.
M.-E. Lebrun, P. Le Marquand, C. Berthelette, J. Org. Chem., 2006, 71, 2009-2013.

Deprotonation of a 64:36 mixture of ethyl bromo(diphenylphosphono)acetate and ethyl dibromo(diphenylphosphono)acetate using NaH as base at 0 °C and subsequent reaction with various aldehydes provided unsaturated α-bromoesters in good yields and high E-selectivities.
T. Olpp, R. Brückner, Synthesis, 2004, 2135-2152.

(E)-β-Arylvinyl bromides were efficiently and stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3-dibromopropanoic acids in AcOH in the presence of AgOAc.
C. Kuang, H. Senboku, M. Tokuda, Tetrahedron, 2005, 61, 637-642.

(Z)-1-Bromo-1-alkenes were stereoselectively efficiently prepared in high yields by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in DMF using Et₃N as base. Microwave-assisted one-pot syntheses of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed.
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Tetrahedron, 2005, 61, 4043-4052.