Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/80539
Title: Triflic-acid-catalyzed tandem allylic substitution–cyclization reaction of alcohols with thiophenols—facile access to polysubstituted thiochromans
Authors: Abdul Sadeer
Pullarkat, Sumod Appukuttan
Shand, Sam S.
Li, Yongxin
Vu, Minh Duy
Foo, Ce Qing
Keywords: Science::Chemistry::Biochemistry
Thiophenols
Thiochromans
Issue Date: 2018
Source: 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
Series/Report no.: ACS Omega
Abstract: 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.
URI: https://hdl.handle.net/10356/80539
http://hdl.handle.net/10220/50371
DOI: http://dx.doi.org/10.1021/acsomega.8b01305
Rights: © 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.
metadata.item.grantfulltext: open
metadata.item.fulltext: With Fulltext
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