Metal-free benzannulation of yne-allenone esters for atom economical synthesis of functionalized 1-naphthols?
Green Chemistry Pub Date: 2018-06-05 DOI: 10.1039/C8GC01034J
Abstract
A new metal-free benzannulation reaction of yne-allenone esters with H2O by using HOAc as a Lewis acid promoter is reported, providing an atom economical protocol toward aroyl 1-naphthols with good to excellent yields. Exchanging H2O for aromatic amines resulted in iminated Z-1-naphthols with high stereoselectivity in a highly functional-group-compatible manner under mild conditions. The purification of these products only needs to be carried out by washing with 95% EtOH solvent, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.
Recommended Literature
- [1] Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications Partha Laskar,Christine DufèsNanoscale Adv., 2021,3, 6007-6026 10.1039/D1NA00536G
- [2] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [3] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [4] Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions? Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng CaiChem. Commun., 2013,49, 11086-11088 10.1039/C3CC46560H
- [5] Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles? Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei YangRSC Adv., 2017,7, 46297-46305 10.1039/C7RA08074C
- [6] Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4? Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di MaRSC Adv., 2018,8, 19353-19361 10.1039/C8RA02762E
- [7] Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon? Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng PuChem. Commun., 2019,55, 3963-3966 10.1039/C9CC01213C
- [8] Ester-mediated peptide formation promoted by deep eutectic solvents: a facile pathway to proto-peptides? Chen-Yu Chien,Sheng-Sheng YuChem. Commun., 2020,56, 11949-11952 10.1039/D0CC03319G
- [9] Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent? Yukiya KitayamaPolym. Chem., 2014,5, 2784-2792 10.1039/C3PY01539D
- [10] Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies Phys. Chem. Chem. Phys., 1999,1, 3561-3565 10.1039/A900683D
Journal Name:Green Chemistry
research_products
-
CAS no.: 89640-58-4