N-Iodosuccinimide (NIS) is an iodinating agent that is used for various electrophilic iodinations and as source for iodine in radical reactions.
Various methoxy- or methyl-substituted aromatic compounds were regioselectively iodinated with N-iodosuccinimide and and a catalytic amount of trifluoroacetic acid with excellent yields under mild conditions and short reaction times.
A.-S. Castanet, F. Colobert, P.-E. Broutin, Tetrahedron Lett., 2002, 43, 5047-5048.
N-Halosuccinimides are efficiently activated in trifluoromethanesulfonic acid and BF3-H2O, allowing the halogenations of deactivated aromatics. BF3-H2O is more economic, easy to prepare, nonoxidizing, and offers sufficiently high acidity.
G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G. A. Olah, J. Am. Chem. Soc., 2004, 126, 15570-15776.
Aryl and heteroaryl boronic acids react with N-iodosuccinimide and N-bromosuccinimide to give the corresponding iodo- and bromo-arenes in good to excellent yields. The reaction is usually highly regioselective and yields only the ipso-substituted product.
C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett, 1998, 141-142.
Reliable, operationally simple, catalytic α-selective hydroalumination reactions proceed in the presence of diisobutylaluminum hydride and (Ni(dppp)Cl2), and, unlike uncatalyzed transformations, generate little or no alkynylaluminum byproducts. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles.
F. Gao, A. H. Hoveyda, J. Am. Chem. Soc., 2010, 132, 10961-10963.
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.
An efficient protocol for a highly stereoselective one-pot synthesis of (E)-β-aryl vinyl iodides and (E)-β-aryl vinyl bromides from styrenes is based on a ruthenium-catalyzed silylative coupling followed by a N-halosuccinimide-mediated halodesilylation reaction.
P. Pawluć, G. Hreczycho, J. Szudkowska, M. Kubicki, B. Marciniec, Org. Lett., 2009, 11, 3390-3393.
A direct asymmetric iodination reaction of aldehydes with NIS catalyzed by a novel axially chiral bifunctional amino alcohol represents a rare example of a highly enantioselective synthesis of optically active α-iodoaldehydes.
T. Kano, M. Ueda, K. Maruoka, J. Am. Chem. Soc., 2008, 130, 3728-3729.
An efficient synthesis of α-iodo/bromo-α,β-unsaturated aldehydes/ketones directly from propargylic alcohols is catalyzed collaboratively by Ph3PAuNTf2 and MoO2(acac)2, and Ph3PO as an additive helps suppress undesired enone/enal formation. Notable features of this method include low catalyst loadings, mild reaction conditions, and mostly good diastereoselectivity.
L. Ye, L. Zhang, Org. Lett., 2009, 11, 3646-3649.
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.
A new silver-catalyzed highly regio- and stereoselective difunctionalization reaction of simple terminal alkynes gives (Z)-β-haloenol acetate derivatives in good yields. The resulting products are versatile intermediates in organic synthesis.
Z. Chen, J. Li, H. Jiang, S. Zhu, Y. Li, C. Qi, Org. Lett., 2010, 12, 3262-3265.
A sequence consisting of an electrophilic cyclization in the presence of N-iodosuccinimide (NIS) and an 1,2-migration allows the construction of 4-iodo-3-furanones from 2-alkynyl-2-silyloxy carbonyl compounds. In a more versatile variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in good yields.
B. Crone, S. F. Kirsch, J. Org. Chem., 2007, 72, 5435-5438.
Various tert-butyldimethylsilyl ethers are easily removed in excellent yields by treatment with a catalytic amount of N-iodosuccinimide in methanol. This method allows a selective deprotection of TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols.
B. Karimi, A. Zamani, D. Zarayee, Tetrahedron Lett., 2004, 45, 9139-9141.
Use of La(OTf)3 as a Lewis acid promoter for N-iodosuccinimide-mediated activation of thioglycosides enables a smooth glycosylation reaction with good to excellent yields and stereoselectivity.
S. Mukherjee, B. Mukhopadhyay, Synlett, 2010, 2853-2856.
Gold(I)-catalyzed cycloisomerization of 1-(2-(tosylamino)phenyl)prop-2-yn-1-ols enables the preparation of 1H-indole-2-carbaldehydes and (E)-2-(iodomethylene)indolin-3-ols in the presence of N-iodosuccinimide (NIS). The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in very good yields.
P. Kothandaraman, S. R. Mothe, S. S. M. Toh, P. W. H. Chan, J. Org. Chem., 2011, 76, 7633-7640.
The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene proceeds smoothly in the presence of electrophilic reagents in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100°C to afford the corresponding quinolines 2 in good to high yields.
Z. Huo, I. D. Gridnev, Y. Yamamoto, J. Org. Chem., 2010, 75, 1266-1270.