Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
Catalytic and Asymmetric Synthesis of Heteroatom-Containing Cyclic Polyarylenes
Takanori Shibata
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2019 Volume 77 Issue 10 Pages 1005-1013

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Abstract

Cyclic polyarylene is a series of compounds, where the cyclic structure is constructed by a number of phenylene and/or heteroarylene moieties. Cyclic polyarylenes consisting of more than three arylene moieties are non-planar, and introduction of substituent(s) induces axial chirality. We comprehensively studied catalytic and enantioselective synthesis of various cyclic polyphenylenes by consecutive inter- and intramolecular cycloadditions of triynes, where 1,6-diyne and alkyne moieties were tethered by phenylene moiety. We further used this strategy for the construction of cyclic heteroarylenes using thiophene-tethered triynes.

Next, we focused on the enantioselective construction of sulfur-containing benzo-fused medium ring systems. For examples, intermolecular cycloaddition of 1,8-diynes tethered by sulfur and two ortho-phenylene moieties with an alkyne gave axially chiral poly-substituted tribenzothiepins possessing a seven-membered ring core. We succeeded in the enantioselective synthesis of seven to eleven-membered benzo-fused compounds by intramolecular reaction of triynes consisting of sulfur-tethered 1,6-diyne and 1, n-diyne moieties (n=8—11).

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© 2019 The Society of Synthetic Organic Chemistry, Japan
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