Phthalimide Derivative for Selective Iodination of Acrylic Esters

N-iodophthalimide (1) is utilized in the selective iodination at the α-position of acrylic esters.¹⁾ When acrylic esters react with 1 in the presence of a catalytic amount of 3-quinuclidinol and KF-Celite under light-shielded conditions, the iodination proceeds via a Morita-Baylis-Hillman type reaction to give α-iodoacrylic esters in good yields. This reaction proceeds only with acrylic esters and not with α,β-unsaturated esters bearing a substituent at the β-position. Given products can be applied in cross couplings such as the Nozaki-Hiyama-Kishi reaction. As per other reports, 1 has also been used as an iodine source in asymmetric iodination reactions.²⁾

Related Product

I1052

N-Iodophthalimide

References

• 1) Highly efficient and chemoselective α-iodination of acrylate esters through Morita–Baylis–Hillman-type chemistry
  • V. Pace, G. Vilkauskaitė, A. Šačkus W. Holzer, Org. Biomol. Chem. 2013, 11, 1085.
• 2) Biomimetic Desymmetrization of a Carboxylic Acid
  • M. T. Knowe, M. W. Danneman, S. Sun, M. Pink, J. N. Johnston, J. Am. Chem. Soc. 2018, 140, 1998.

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