Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans
Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that al...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2019
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| Online Access: | https://hdl.handle.net/10356/80539 http://hdl.handle.net/10220/50371 |
| _version_ | 1826126170072023040 |
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| author | Abdul Sadeer Pullarkat, Sumod Appukuttan Shand, Sam S. Li, Yongxin Vu, Minh Duy Foo, Ce Qing |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Abdul Sadeer Pullarkat, Sumod Appukuttan Shand, Sam S. Li, Yongxin Vu, Minh Duy Foo, Ce Qing |
| author_sort | Abdul Sadeer |
| collection | NTU |
| description | Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that allows the introduction of up to four substituents at various locations on the thiochroman skeleton. Relative conformations of all isolated products were confirmed by NOESY NMR studies, and a stepwise mechanism, proceeding via an allylic substitution-intramolecular cyclization protocol, is proposed on the basis of NMR experiments. |
| first_indexed | 2024-10-01T06:48:19Z |
| format | Journal Article |
| id | ntu-10356/80539 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:48:19Z |
| publishDate | 2019 |
| record_format | dspace |
| spelling | ntu-10356/805392023-02-28T19:28:47Z Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans Abdul Sadeer Pullarkat, Sumod Appukuttan Shand, Sam S. Li, Yongxin Vu, Minh Duy Foo, Ce Qing School of Physical and Mathematical Sciences Science::Chemistry::Biochemistry Thiophenols Thiochromans Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that allows the introduction of up to four substituents at various locations on the thiochroman skeleton. Relative conformations of all isolated products were confirmed by NOESY NMR studies, and a stepwise mechanism, proceeding via an allylic substitution-intramolecular cyclization protocol, is proposed on the basis of NMR experiments. Published version 2019-11-07T06:31:26Z 2019-12-06T13:51:46Z 2019-11-07T06:31:26Z 2019-12-06T13:51:46Z 2018 Journal Article Vu, M. D., Foo, C. Q., Abdul Sadeer., Shand, S. S., Li, Y., & Pullarkat, S. A. (2018). Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans. ACS Omega, 3(8), 8945-8951. doi:10.1021/acsomega.8b01305 https://hdl.handle.net/10356/80539 http://hdl.handle.net/10220/50371 10.1021/acsomega.8b01305 en ACS Omega © 2018 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. 7 p. application/pdf |
| spellingShingle | Science::Chemistry::Biochemistry Thiophenols Thiochromans Abdul Sadeer Pullarkat, Sumod Appukuttan Shand, Sam S. Li, Yongxin Vu, Minh Duy Foo, Ce Qing Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title | Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title_full | Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title_fullStr | Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title_full_unstemmed | Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title_short | Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans |
| title_sort | triflic acid catalyzed tandem allylic substitution cyclization reaction of alcohols with thiophenols facile access to polysubstituted thiochromans |
| topic | Science::Chemistry::Biochemistry Thiophenols Thiochromans |
| url | https://hdl.handle.net/10356/80539 http://hdl.handle.net/10220/50371 |
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