261907-32-8Relevant articles and documents
The formation of 1-aryl-substituted naphthalenes by an unusual cyclization of arylethynes catalyzed by ruthenium and rhodium porphyrins
Elakkari, Elfituri,Floris, Barbara,Galloni, Pierluca,Tagliatesta, Pietro
, p. 889 - 894 (2005)
The dimerization of arylethynes to give 1-aryl-substituted naphthalenes through catalysis by rhodium and ruthenium porphyrins has been investigated. When performed at temperatures above 130 °C, this reaction affords a mixture of triarylbenzenes and 1-aryl-substituted naphthalenes. The yields of naphthalene derivatives range from low to high, depending on the temperature and the phenyl substituents. The concentrations of the initial compounds affect the selectivity of the reaction: the dimerization/trimerization ratios in 1,2-dichlorobenzene increase as concentration decreases. The reaction mechanism is determined by the peculiar structure of the catalyst ligand and involves the formation of a vinylidene intermediate of the metalloporphyrins. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Fe-Catalyzed Intramolecular Cross-Dehydrogenative Arylation (CDA), Efficient Synthesis of 1-Arylnaphthalenes and 4-Arylcoumarins
Diao, Haiyan,Wang, Changcheng,Zhang, Zhen,Shi, Zhangjie,Liu, Feng
, (2021/06/27)
Direct cross-dehydrogenative coupling of different inert C?H bonds is the most straightforward and environmentally benign method to construct C?C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp3)H bond and aromatic C(sp2)H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization-dehydrogenation tandem process was proposed.
Regioselective synthesis of substituted naphthalenes and phenanthrenes by FeCl3-promoted annulation of aryl and naphthyl acetaldehydes with alkynes
Bu, Xiuli,Hong, Longcheng,Liu, Ruiting,Hong, Jianquan,Zhang, Zhengxing,Zhou, Xigeng
experimental part, p. 7960 - 7965 (2012/09/21)
The FeCl3-promoted annulation reaction of aryl acetaldehydes with alkynes has been established, which provides a new and versatile straightforward procedure for the regioselective synthesis of mono-, di-, and polysubstituted naphthalenes under mild conditions. Interestingly, the present catalytic system not only differentiates between internal and terminal alkynes but also shows unprecedented complete Me3SiOH elimination selectivity for silyl alkyne substrates. Furthermore, the synthesis of a series of substituted phenanthrenes via reactions of nathphyl acetaldehydes with internal alkynes is also achieved for the first time in good yields with excellent regioselectivity.
Ruthenium porphyrin bound to a Merrifield resin as heterogeneous catalyst for the cyclooligomerization of arylethynes
Ciammaichella, Alina,Leoni, Alessandro,Tagliatesta, Pietro
scheme or table, p. 2122 - 2124 (2011/01/06)
Ruthenium meso-tetraphenylporphyrin was bound to a solid support, the Merrifield resin, and used in the cyclooligomerization of arylethynes, obtaining high yields and selectivities in the final products with a complete recycling of the catalyst.
The highly selective formation of biaryls by the cyclization of arylethynes catalyzed by vanadyl phthalocyanine
Cicero, Daniel,Lembo, Angelo,Leoni, Alessandro,Tagliatesta, Pietro
experimental part, p. 2162 - 2165 (2009/12/25)
The dimerization of arylethynes catalyzed by vanadium phthalocyanine to give substituted biaryls has been investigated. The reaction yield is always high and for many examples is only slightly affected by the aryl substituents. This fact is also related to the results obtained with metalloporphyrins, which give lower selectivities due to the presence of variable amounts of triphenylbenzenes.
