Synthesis of vinyl iodides

Recent Literature

A mild and general copper(I)-catalyzed conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed. Various functional groups and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions.
A. Klapars, S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 14844-14845.

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.

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.

A catalytic amount of Au(PPh₃)NTf₂ converts readily accessible propargylic acetates into versatile linear α-iodoenones in good to excellent yields. Very good Z-selectivities are observed for aliphatic propargylic acetates.
M. Yu, G. Zhang, L. Zhang, Org. Lett., 2007, 9, 2087-2090.

γ-Hydroxy-α,β-acetylenic esters are used as precursors for the preparation of γ-hydroxy-α,β-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow the preparation of β-substituted and α,β-disubstituted alkenoic esters in highly stereoselective manners.
C. T. Meta, K. Koide, Org. Lett., 2004, 6, 1785-1787.

Various ketones as the electrophiles react in a one pot three-component coupling with an aluminum allenoate intermediate derived from ethyl propiolate and alluminium iodide to yield β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity.
S. Il Lee, G.-S. Hwang, D. H. Ryu, Synlett, 2007, 59-62.

A simple and highly stereoselective method has been developed for the synthesis of (Z)-β-iodo Baylis-Hillman adducts using CeCl₃·7H₂O/NaI as an inexpensive and readily available reagent system.
J. S. Yadav, B. V. S. Reddy, M. K. Gupta, B. Eeshwaraiah, Synthesis, 2005, 57-60.

A new, diastereoselective three-component halo aldol reaction has been discovered for the tandem formations of I-C/C-C bonds, which gives aldol adducts in good yields. The key intermediates (allenolates and 1-iodo-3-siloxy-1,3-butadienes), were directly monitored by ¹H NMR.
H.-X. Wei, S. H. Kim, G. Li, Org. Lett., 2002, 4, 3691-3693.

A mild, electrophilic cyclization of substituted propargylic aryl ethers by I₂, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology tolerates various functional groups, such as methoxy, alcohol, aldehyde, and nitro groups.
S. A. Worlikar, T. Kesharwani, T. Yao, R. C. Larock, J. Org. Chem., 2007, 72, 1347-1353.

Iodocyclopentenes are formed at room temperature upon iodonium-promoted 5-endo-dig carbocyclization of δ-alkynyl-β-ketoesters with I₂. Cyclizations involving terminal and substituted (alkyl, aryl, Br, I) alkynes were accessed.
J. Barluenga, D. Palomas, E. Rubio, J. M. Gonzáles, Org. Lett., 2007, 9, 2823-2826.

The facile iodolactonisation of ethyl 2,3-allenoates with I₂ in aqueous MeCN gave 4-iodofuran-2(5H)-ones in moderate to high yields.
C. Fu, S. Ma, Eur. J. Org. Chem., 2005, 3942-3945.

Lithiation of 1-iodo-1,3-dienyl phosphine oxides and subsequent Wittig-Horner reaction with aldehydes gives vinyl allenes in high yields. The preparation of the 1-iodo-1,3-dienyl phosphine oxides is described. This multi-step sequence allows the synthesis of vinyl allenes from two different alkynes and one aldehyde.
Z. Xi, W.-X. Zhang, Z. Song, W. Zheng, F. Kong, T. Takahashi, J. Org. Chem., 2005, 70, 8785-8789.

The cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate afforded the corresponding acetylenic sulfones in high yields.
V. Nair, A. Augustine, T. D. Suja, Synthesis, 2002, 2259-2265.

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.