Substrate‐Controlled Hydrogenation of Flavanones: Selective Synthesis of 2′‐Hydroxy‐1, 3‐Diarylpropanes and Flavans. Issue 16 (29th March 2023)

• Record Type: Journal Article
• Authors: Soto, Martín; Pérez‐Ramos, Paula; Soengas, Raquel G.; Rodríguez‐Solla, Humberto
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 16(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-03-29
• Subjects: diarylpropanes -- flavans -- green solvents -- hydrogenation -- palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202300139
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new substrate‐controlled hydrogenation of flavanones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of flavanones bearing different electron‐donating and electron withdrawing substituents (Cl, Br, Me, OMe, OH) provided the corresponding 1, 3‐diarylpropanes in excellent yields. This procedure offers a straightforward, simple, and cost‐effective method for the preparation of glycosylated 2′‐hydroxy‐1, 3‐diarylpropanes derived from natural flavanones such as Naringin and Hesperedin. On the contrary, when the hydrogenation was performed over fluorinated flavanones, the corresponding flavans were selectively obtained in excellent yields. Abstract : Herein, a new substrate‐controlled hydrogenation of flavanones to selectively obtain 2′‐hydroxy‐1, 3‐diarylpropanes or flavans depending on the substitution of the flavanone moiety is described. Thus, hydrogenation of non‐fluorinated flavanones provided the corresponding 2′‐hydroxy‐1, 3‐diarylpropanes, whereas hydrogenation of fluorinated flavanones afforded selectively the corresponding flavans in excellent yields.