Methods for preparing substituted chromanone derivatives

A method for preparing a compound of formula (XII)

• or an enantiomer of the compound of formula (XII), wherein n is 0 to 5, each of R1, R2, R3, and R4 is independently selected from the group consisting of H, —O-Alkyl, halo, alkyl, —CN, or —NO3, and the method comprises:
• treating a compound of formula (III),
• wherein X is halo, with a compound of formula (IV),
• wherein R5 is H, —CH3 or —CH2CH3, in the presence of a catalyst and a base, wherein the catalyst includes a ligand and a copper compound, to obtain a compound of formula (II),
• treating the compound of formula (II) with 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) in the presence of NaClO and NaClO2 to obtain a compound of formula (XI);
• treating the compound of formula (XI) with concentrated sulfuric acid to obtain a compound of formula (I);
• and
• treating the compound of formula (I) with a hydrogen donor in the presence of a catalyst to obtain the compound of formula (XII),
• or the enantiomer of the compound of formula (XII).