@article{RiemerShipmanWessigetal.2019,
  author    = {Riemer, Nastja and Shipman, Michael and Wessig, Pablo and Schmidt, Bernd},
  title     = {Iterative arylation of itaconimides with diazonium salts through electrophilic palladium catalysis},
  series = {The journal of organic chemistry},
  volume    = {84},
  journal   = {The journal of organic chemistry},
  number    = {9},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.9b00627},
  pages     = {5732 -- 5746},
  year      = {2019},
  abstract  = {N-Arylitaconimides, accessible from maleic anhydride, anilines, and paraformaldehyde, react with arene diazonium salts in Pd-catalyzed Matsuda-Heck arylation to the pharmacologically relevant E-configured 3-arylmethylidene pyrrolidine-2,5-diones (also known as arylmethylidene succinimides) through exo-selective beta-H-elimination. The coupling proceeds at ambient temperature with the simple and easy-to-handle precatalyst Pd-II-acetate under ligandand base-free conditions. Notable features are high isolated yields, regio- and stereoselectivities, and short reaction times. In a comparative investigation, aryl iodides, bromides, and triflates were shown to be inferior coupling reagents in this reaction. The 3-arylmethylidene pyrrolidine-2,5-diones undergo second Matsuda-Heck coupling, which proceeds via endo-selective beta-H-elimination to give diarylmethyl-substituted maleimides as coupling products. These products can also be accessed in one flask by sequential addition of different arene diazonium salts to the starting itaconimide. The potential of 3-arylmethylidene succinimides as photoswitches was tested. Upon irradiation of the E-isomer at 300 nm, partial isomerization to the Z-isomer (E/Z = 65:35 in the photostationary state) was observed. The isomerization was found to be nearly completely reversible by irradiating the mixture at 400 nm.},
  language  = {en}
}