Synthesis of vinyl chlorides

Recent Literature

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.

The reaction of aromatic ketones with bis(trichloromethyl) carbonate afforded aryl-(Z)-vinyl chlorides in the presence of scandium triflate, DMF, and benzoyl chloride as catalysts. A plausible addition-elimination mechanism is proposed. This catalytic method enables a green route to aryl-(Z)-vinyl chlorides.
W. Su, C. Jin, Org. Lett., 2007, 9, 993-996.

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.

Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides under Moffatt-Swern Conditions using excess DMSO and oxalyl chloride or oxalyl bromide. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide.
J. Yin, C. E. Gallis, J. D. Chisholm, J. Org. Chem., 2007, 72, 7054-7057.

2-Alkynyl esters are stereo- and regioselectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu₄NI in refluxing dichloroethane. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions.
A. B. Lemay, K. S. Vulic, W. W. Ogilvie, J. Org. Chem., 2006, 71, 3615-3618.

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.

The use of bisphosphine ligands with a large P-Pd-P bite angle allowed to synthesize Z-chlorinated internal alkenes in good yields by a selective Suzuki-Miyaura monocoupling process of 9-alkyl-9-BBN with 1,1-dichloro-1-alkenes. These monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.
F. Liron, C. Fosse, A. Pernolet, E. Roulland, J. Org. Chem., 2007, 72, 2220-2223.