Copper-Promoted C–Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

Abstract

The modification of Chan–Lam–Evans cross-coupling reaction for the selective Se-arylation of 2-selenohydantoins under base-free mild conditions via aryl boronic acids is described herein. This approach was used to synthesize novel 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones with high yields. The anticancer activity of the final compounds was evaluated in vitro against different cancer cells, and thus, the possibility of 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones successful application as cytotoxic agents was demonstrated.

Ullmann-type C–Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity

“…As the next logical step after boronic acid-based crosscoupling, 32 we took (Table 1) the same disubstituted 2selenohydantoin 1a (1 equiv) but now with iodobenzene 2a (2−3 equiv) for the optimization of reaction conditions. First, we tried copper(I) iodide as a typical copper source for Ullmann-type 33 reactions and sodium tert-butoxide as a base.…”

“…The chemoselectivity for iodine is outstanding; no other halides react. Thus, the new Ullmann-type approach is complementary to the Chan−Evans−Lam-type approach, 32 as seen for the heteroarylated selenohydantoins 3apy−3apyr. 2 The functional group tolerance is good (Scheme 2); substituents like CN, COOMe, RNHC(O)Me, CO, and ferrocene core give yields up to 88%.…”

“…We have extended the Chan−Evans−Lam reaction to C−Se bonds by coupling 2-selenohydantoins 1 with arylboronic acids, 32 which often works under mild conditions with good yields (Figure 1), but less so for boronic acids bearing electronwithdrawing groups, and fails for heteroarylboronic acids and 5-alkylidine-3-substituted-2-selenohydantoinsa class of promising targets.…”

Copper coordination compounds with (5Z,5Z′)-2,2′-(alkane-α,ω-diyldiselenyl)-bis-5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones. Comparison with sulfur analogue

“…Selenium-containing ligands 4a-k were obtained by the reaction sequence shown in Scheme 1, starting from ethyl isoselenocyanatoacetate and the corresponding alkyl or aryl amines. Compounds 1, 2a-d and 3c,d have been previously described; 34,35 compounds 3a and 3b were synthesized in the same way (see ESI †).…”

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

“…In 2019, Finko and co-workers reported the selective Searylation of 2-selenohydantoins using arylboronic acids under base-free mild conditions (Scheme 147). 116 The strategy was used in the synthesis of novel 3-substituted 5arylidene-2-(arylseleno)imidazolin-4-ones in high yields.…”