61714-10-1Relevant articles and documents
Hydroxyl Assisted, Photoredox/Cobalt Co-catalyzed Semi-Hydrogenation and Tandem Cyclization of o-Alkynylphenols for Access to 2,3-Dihydrobenzofurans
Tian, Wan-Fa,Zhu, Yao,He, Yong-Qin,Wang, Mei,Song, Xian-Rong,Bai, Jiang,Xiao, Qiang
supporting information, p. 730 - 736 (2020/12/15)
Herein, a hydroxyl assisted, photoredox/cobalt co-catalyzed semi-hydrogenation and tandem cyclization of o-alkynylphenols is developed towards direct assembly of 2,3-dihydrobenzofurans. Moderate to good yields were obtained for a range of sterically and electronically diverse 2-propynolphenols under mild conditions. Mechanistic studies demonstrated the inevitable role of the alcoholic hydroxyl group with (Z)-alkene as the real intermediate. Finally, a key low-valent cobalt catalyzed intramolecular hydroetherification of alkene is proposed. (Figure presented.).
Reaction of 3-Halogeno-2H-1-benzopyran-2-ones with Organometallic Compounds. Synthesis of 4-Alkyl-2H-1-benzopyran-2-ones. X-Ray Molecular Structure of 3-Bromo-3,4-dihydro-4-isopropylcoumarin
Alberola, Angel,Calvo, Blanca,Ortega, Alfonso Gonzalez,Vicente, Martina,Granda, Santiago G.,Van der Maelen, Juan F.
, p. 203 - 210 (2007/10/02)
3-Halogeno-2H-1-benzopyran-2-ones react with magnesium, lithium, aluminium and copper derivatives to give 3,4-dihydrocuomarins and 3-(o-hydroxyphenyl)propenols as major products.The nature and the ratio of the products in the final mixture depend on the solvent and on the organometallic reagent.Grignard derivatives yield 1,4-monoalkylation compounds in tetrahydrofuran (THF) or 1,2-dialkylation derivatives in toluene.In some cases the dehalogenation competes with the 1,2-alkylation process in the reactions with alkyllithiums.The presence of the halogen at C-3 increases the reductive ability of organoaluminiums.In general, the reaction with lithium dialkylcuprates leads to complex mixtures of products.The 4-alkyl-3-halogeno-3,4-dihydrocuomarins obtained undergo dehydrohalogenation easily, and lead to 4-alkylcuomarins in good yields.The tandem alkylation-dehydrohalogenation of 3-halogeno-2H-1-benzopyran-2-ones constitutes a versatile synthesis of 4-alkylcuomarins.