Triflic-Acid-Catalyzed Tandem Allylic Substitution–Cyclization Reaction of Alcohols with Thiophenols—Facile Access to Polysubstituted Thiochromans | Zendy

Minh Duy Vu | Zendy; Ce Qing Foo | Zendy; Abdul Sadeer | Zendy; Sam S. Shand | Zendy; Yongxin Li | Zendy; Sumod A. Pullarkat | Zendy

Open Access

Triflic-Acid-Catalyzed Tandem Allylic Substitution–Cyclization Reaction of Alcohols with Thiophenols—Facile Access to Polysubstituted Thiochromans

Author(s) -

Minh Duy Vu,

Ce Qing Foo,

Abdul Sadeer,

Sam S. Shand,

Yongxin Li,

Sumod A. Pullarkat

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b01305

Subject(s) - allylic rearrangement , triflic acid , intramolecular force , catalysis , chemistry , tandem , combinatorial chemistry , substitution (logic) , organic chemistry , stereochemistry , computer science , materials science , composite material , programming language

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.

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