Solvent‐Controlled Hydrogenation of 2'‐Hydroxychalcones: A Simple Solution to the Total Synthesis of Bussealins. Issue 23 (1st October 2020)

• Record Type: Journal Article
• Authors: Soto, Martín; Soengas, Raquel G.; Rodríguez‐Solla, Humberto
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 23(2020)
• Page Start: 5422
• Page End: 5431
• Publication Date: 2020-10-01
• Subjects: Bussealins -- Chalcones -- Green Solvents -- Hydrogenation -- Palladium; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000892
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A solvent‐controlled hydrogenation of 2'‐hydroxychalcones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of 2'‐hydroxychalcones using EtOH as solvent provided the corresponding 1, 3‐diarylpropanes in excellent yields. On the contrary, when the hydrogenation was performed in DCM, the corresponding dihydrochalcones were isolated. Switching the reaction solvent to n ‐BuOH/H2 O (1:1), afforded 1, 3‐diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost‐effective method for the preparation of a wide variety of 2'‐hydroxy‐1, 3‐diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D. Abstract :