Denitrative thiocyanation of β-nitrostyrenes through visible light photoredox catalysis: An easy access to (E)-vinyl thiocyanates

Eosin Y mediated photo-catalytic C–H functionalization: C–C and C–S bond formation

“…Recently, they developed a methodology to catalyze the aerobic photoinduced formation of the C–S bond via denitration of β-nitrostyrene ( 158 ) using ammonium thiocyanate to give ( E )-vinylthiocyanates ( 159 ) in up to 87% yield (Scheme 75). 71 Substitution at the different positions of the aryl ring with electron-donating groups showed tunning with the reaction and gave the corresponding compounds in good yields. However, substitution with electron-withdrawing groups only at the ortho -position gave compounds in moderate to good yields, while substitution at the meta - and - para positions with these groups gave lower yields of the final compounds.…”

Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation

“…Kapoor et al demonstrated the photocatalytic denitrative thiocyanation of β-nitrostyrenes 25. 16 They employed EY as a photocatalyst and ammonium thiocyanate as a thiocyanating agent in acetonitrile as an organic solvent in open air under visible light to create ( E )-vinyl thiocyanates 26 in excellent to outstanding yields ( Scheme 9a ). They proposed that visible light stimulates EY, which then uses the SET mechanism to oxidize thiocyanate anion B to SCN radical B′ through a reductive quenching circle.…”

Visible Light‐Mediated Reactions of β‐Nitroalkenes

“…In 2020, Yadav and co‐workers reported the synthesis of vinyl thiocyanates 19 from nitroalkenes 1 via denitrative thiocyanation reaction catalyzed by photo‐induced eosin Y (Scheme 16). [60] The reaction was performed in acetonitrile solvent in presence of aerobic oxygen. The reaction conditions were thoroughly stabilized and a variety of nitroalkenes 1 were screened under optimized conditions.…”