Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]
A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (Tf...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.35 |
| _version_ | 1819203754554032128 |
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| author | Takeshi Fujita Noriaki Shoji Nao Yoshikawa Junji Ichikawa |
| author_facet | Takeshi Fujita Noriaki Shoji Nao Yoshikawa Junji Ichikawa |
| author_sort | Takeshi Fujita |
| collection | DOAJ |
| description | A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes. |
| first_indexed | 2024-12-23T04:24:57Z |
| format | Article |
| id | doaj.art-a2db5ef1a6b84788989bfb897daccca4 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-23T04:24:57Z |
| publishDate | 2021-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a2db5ef1a6b84788989bfb897daccca42022-12-21T18:00:09ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117139640310.3762/bjoc.17.351860-5397-17-35Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]Takeshi Fujita0Noriaki Shoji1Nao Yoshikawa2Junji Ichikawa3Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, JapanDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, JapanDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, JapanDivision of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, JapanA facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.https://doi.org/10.3762/bjoc.17.35acidcatalystcyclizationfluoroalcoholhelicenes |
| spellingShingle | Takeshi Fujita Noriaki Shoji Nao Yoshikawa Junji Ichikawa Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] Beilstein Journal of Organic Chemistry acid catalyst cyclization fluoroalcohol helicenes |
| title | Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] |
| title_full | Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] |
| title_fullStr | Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] |
| title_full_unstemmed | Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] |
| title_short | Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH] |
| title_sort | helicene synthesis by bronsted acid catalyzed cycloaromatization in hfip cf3 2choh |
| topic | acid catalyst cyclization fluoroalcohol helicenes |
| url | https://doi.org/10.3762/bjoc.17.35 |
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