Electrophilic Oxythio/selenocyanation of o‐Alkenyl Benzoic Acids: Divergent Synthesis of Thio/selenocyanated Isobenzofuranones and Isocoumarins

A transition‐metal free thio/selenocyanation of o‐alkenyl benzoic acids via the electrophilic Cl−S(Se)CN species, in‐situ generated from inorganic thio/selenocyanating salt and PhICl2, has been realized under mild reaction conditions. This protocol offers a divergent synthesis of thio/selenocyanated...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2022-12, Vol.11 (12), p.n/a
Main Authors: Tao, Shanqing, Jiang, Luchen, Du, Yunfei
Format: Article
Language:English
Subjects:
Benzoic acid
Isobenzofuranone
Isocoumarin
o-Alkenyl Benzoic Acid
Organic chemistry
Oxyselenocyanation
Oxythiocyanation
Substitution reactions
Substrates
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Summary:A transition‐metal free thio/selenocyanation of o‐alkenyl benzoic acids via the electrophilic Cl−S(Se)CN species, in‐situ generated from inorganic thio/selenocyanating salt and PhICl2, has been realized under mild reaction conditions. This protocol offers a divergent synthesis of thio/selenocyanated isobenzofuranones and isocoumarins, depending on the substitution type of the substrates. A divergent synthesis of the biologically interesting thio/seleocyanated isobenzofuranones and isocoumarins was realized by reacting o‐alkenyl benzoic acids with PhICl2 under mild reaction conditions. An ionic mechanistic pathway involving the in situ generated electrophilic species Cl−SCN/Cl−SeCN was postulated.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200595