Iodine

Name Reactions

Recent Literature

A zinc carbenoid-mediated chain extension of β-dicarbonyl compounds provides access to α,β-unsaturated-γ-keto esters and amides with complete E selectivity via an intermediate zinc enolate, which is treated sequentially with iodine and DBU.
M. D. Ronsheim, C. K Zercher, J. Org. Chem., 2003, 68, 4535-4538.

A new, green, mild and inexpensive system, I₂-KI-K₂CO₃-H₂O, selectively oxidized alcohols to aldehydes and ketones under anaerobic condition in water at 90 °C with excellent yields.
P. Gogoi, D. Konwar, Org. Biomol. Chem., 2005, 3, 3473-3475.

Iodine was compared to other positive halogens as terminal oxidant in chemoselective oxidations of alcohols using catalytic TEMPO and was shown to be superior in cases of electron-rich and heteroaromatic benzylic alcohols.
R. A. Miller, R. S. Hoerrner, Org. Lett., 2003, 5, 285-287.

A simple, efficient, and high-yield procedure for the oxidative conversion of alcohols to various types of esters and ketones was successfully carried out with molecular iodine as the oxidant and potassium carbonate.
N. Mori, H. Togo, Tetrahedron, 2005, 61, 5915-5925.

N. Mori, H. Togo, Tetrahedron, 2005, 61, 5915-5925.

2-Imidazolines were easily prepared in good yields from the reaction of aldehydes and ethylenediamine with iodine in the presence of potassium carbonate. The 2-imidazolines were smoothly oxidized to the corresponding imidazoles in good yields using (diacetoxyiodo)benzene at room temperature.
M. Ishihara, H. Togo, Synlett, 2006, 227-230.

A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford the corresponding triazines and tetrazoles in high yields.
J.-J. Shie, J.-M. Fang, J. Org. Chem., 2007, 72, 3141-3144.

J.-J. Shie, J.-M. Fang, J. Org. Chem., 2007, 72, 3141-3144.

Iodine efficiently catalyzes the three-component coupling of aromatic aldehydes, enolizable ketones or keto esters, and acetonitrile in the presence of acetyl chloride at room temperature to afford β-acetamido ketones in good yields.
B. Das, K. Ravinder Reddy, R. Ramu, P. Thirupathi, B. Ravikanth, Synlett, 2006, 1756-1758.

An efficient and mild thiophenol-promoted ring-opening of aziridines or epoxides with iodine afforded β-iodo amines or β-iodo alcohols in very good yields.
J. Wu, X. Sun, W. Sun, S. Ye, Synlett, 2006, 2489-2491.