Visible-Light-Mediated Decarboxylative Thiocyanation of Cinnamic acids: An Efficient Photocatalytic Approach to the Synthesis of (E)-Vinyl Thiocyanates

A simple and novel methodology for the synthesis of vinyl thiocyanates from decarboxylative cross-coupling reaction of cinnamic acids with KSCN under the synergistic interactions of visible light irradiation, Cs 2 CO 3 , Rose Bengal as the photocatalyst and air as the terminal oxidant at room temper...

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Bibliographic Details
Published in:Catalysis letters 2021-06, Vol.151 (6), p.1738-1744
Main Authors: Jaiswal, Deepali, Tiwari, Jyoti, Singh, Shailesh, Kartikey, Singh, Jaya, Singh, Jagdamba
Format: Article
Language:English
Subjects:
Catalysis
Chemical reactions
Chemistry
Chemistry and Materials Science
Cinnamic acid
Cross coupling
Industrial Chemistry/Chemical Engineering
Light irradiation
Organometallic Chemistry
Oxidizing agents
Photocatalysis
Physical Chemistry
Room temperature
Sulfur compounds
Thiocyanates
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Summary:A simple and novel methodology for the synthesis of vinyl thiocyanates from decarboxylative cross-coupling reaction of cinnamic acids with KSCN under the synergistic interactions of visible light irradiation, Cs 2 CO 3 , Rose Bengal as the photocatalyst and air as the terminal oxidant at room temperature is reported. The reaction takes place by a radical pathway as evidenced from our experiments and literature. The report is the first example on the visible-light mediated thiocyanation of cinnamic acids, which employs environmentally benign and inexpensive starting materials and is characterized by easily removable by-product CO 2 . Graphic Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-020-03414-6