Practical synthesis of [n]cycloparaphenylenes (n = 5, 7-12) by H2SnCl4-mediated aromatization of 1,4-dihydroxycyclo-2,5-diene precursors

Chemistry : a European Journal
Vijay Kumar PatelShigeru Yamago

Abstract

Cyclic precursors of cycloparaphenylenes (CPPs) containing 1,4-dihydroxy-2,5-cyclohexadien-1,4-diyl units are prepared by modifying a synthetic method developed by Jasti and co-workers for the synthesis of corresponding 1,4-dimethoxy derivatives. Reductive aromatization of the diyl moieties by SnCl2/2 HCl takes place under mild conditions and affords the CPPs in good yields, incorporating 5 or 7-12 phenylene units. Highly strained [5]CPP is synthesized in greater than 0.3 g scale. (119)Sn NMR spectroscopy clarifies the in situ formation of an ate complex, H2SnCl4, upon mixing a 2:1 ratio of HCl and SnCl2, which serves as a highly active reducing agent under nearly neutral conditions. When more than 2 equivalents of HCl, in relation to SnCl2, are used, acid-catalyzed decomposition of the CPP precursors takes place. The stoichiometry of HCl and SnCl2 is critical in achieving the desired aromatization reaction of highly strained CPP precursors.

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Citations

May 11, 2016·ACS Central Science·Evan R DarziRamesh Jasti
Mar 24, 2016·Organic Letters·Penghao LiRamesh Jasti
May 3, 2016·Journal of the American Chemical Society·Matthew R GolderRamesh Jasti
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Jun 28, 2018·Chemical Communications : Chem Comm·Sarah N SpisakMarina A Petrukhina
Oct 17, 2018·Angewandte Chemie·Tobias A SchaubRamesh Jasti
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May 4, 2016·Chemistry, an Asian Journal·Eiichi KayaharaShigeru Yamago
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Jul 1, 2017·ChemPlusChem·Sigma HashimotoShigeru Yamago
Feb 19, 2016·Angewandte Chemie·Yasutomo SegawaKenichiro Itami
Jan 13, 2018·Chemistry, an Asian Journal·Kiyonori KurodaMichito Yoshizawa
Feb 19, 2021·Angewandte Chemie·Zeming XiaQian Miao
Mar 23, 2020·Chemical Science·Curtis E ColwellRamesh Jasti
Nov 12, 2019·Journal of the American Chemical Society·Youzhi XuMax von Delius
Dec 1, 2017·Journal of the American Chemical Society·Eiichi KayaharaShigeru Yamago
Sep 14, 2018·Organic Letters·Sigma HashimotoShigeru Yamago
Apr 19, 2019·Journal of the American Chemical Society·Kabali SenthilkumarMarcin Stępień

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