106593-25-3Relevant academic research and scientific papers
Ruthenium-catalyzed rearrangement of cis-1-ethynyl-2-vinyloxiranes to substituted phenols
Maddirala, Shambabu Joseph,Odedra, Arjan,Taduri, Bhanu Pratap,Liu, Rai-Shung
, p. 1173 - 1176 (2006)
Catalytic cyclization of cis-1-ethynyl-2-vinyloxiranes was implemented with TpRuPPh3(CH3CN)2PF6 catalyst (10 mol%), to give 2,6-disubstituted phenols in reasonable yields. Under similar conditions, 1,1,2,2-tetrasubstituted oxirane gave the 2,3,6-trisubstituted phenol with skeleton reorganization. On the basis of 2H- and l3C-labeling results, we propose that the reaction mechanism involves electrocyclization of ruthenium-vinylidene intermediate with cleavage of the carbon-oxygen bond of the epoxide. Georg Thieme Verlag Stuttgart.
Palladium-catalyzed aerobic synthesis of: Ortho -substituted phenols from cyclohexanones and primary alcohols
Zeng, Huiying,Yu, Jianjin,Li, Chao-Jun
supporting information, p. 1239 - 1242 (2020/02/04)
Due to the importance of phenols as structural cores and precursors of chemical products, synthesis of site-specific substituted phenols is highly desirable and a significant challenge. An aerobic palladium-catalyzed site-specific synthesis of ortho-substituted phenols from cyclohexanones and primary alcohols via an oxidation/aldol/dehydration/aromatization process has been developed. Various substituted cyclohexanones and primary alcohols are successfully transformed into ortho-substituted phenols. In addition, this catalytic reaction uses air as the terminal oxidant and generates water as the sole by-product. Furthermore, the method can also be extended to polyhydroxyl substituted substrates with high chemoselectivity between primary and secondary alcohols. This method provides a greener tool for synthesizing primary alkyl ortho-substituted phenols.
