- Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) via a Transient Directing Group
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In this work, an efficient synthetic route was developed to construct PAHs with diverse shape, width, and edge topology. The precursors of PAHs were obtained by using a direct arylation of arenes via a transient ligand-directed C-H functionalization strategy and the cycloaromatization was readily achieved by using a Br?nsted acid catalyst. This novel route provides an opportunity to build up PAHs in a highly efficient manner.
- Tang, Ming,Yu, Qinqin,Wang, Ziqi,Zhang, Chen,Sun, Bing,Yi, Ying,Zhang, Fang-Lin
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supporting information
p. 7620 - 7623
(2018/12/11)
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- Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds
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Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright
- Xia, Ying,Liu, Zhenxing,Xiao, Qing,Qu, Peiyuan,Ge, Rui,Zhang, Yan,Wang, Jianbo
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p. 5714 - 5717
(2012/07/28)
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- A Rapid, Convergent, and Regioselective Synthesis of Anthracenes
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Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran.In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes.Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole.For example, the only trimethoxyanthracene isolated (48percent yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20.When 1,2-dihydrocyclobutaphenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenzanthracene in 68percent yield from 14 and bromonaphthalene.In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.
- Fitzgerald, John J.,Drysdale, Neville E.,Olofson, R. A.
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p. 7122 - 7126
(2007/10/02)
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