Copper-catalyzed double C-S bond formation for the synthesis of 2-acyldihydrobenzo[]thiophenes and 2-acylbenzo[]thiophenes

An efficient domino process is developed for the synthesis of diversely substituted 2,3-dihydrobenzo[ b ]thiophenes from 2-iodoketones using a Cu-catalyst and easily available xanthate as a sulfur surrogate in good yields. This domino method has been expanded for the synthesis of 2-acylbenzo[ b ]thi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-09, Vol.56 (74), p.196-199
Main Authors: Sangeetha, Subramani, Sekar, Govindasamy
Format: Article
Language:English
Subjects:
Catalysts
Copper
Copper compounds
Crystallography
Iodine
Thiophenes
X ray photoelectron spectroscopy
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Summary:An efficient domino process is developed for the synthesis of diversely substituted 2,3-dihydrobenzo[ b ]thiophenes from 2-iodoketones using a Cu-catalyst and easily available xanthate as a sulfur surrogate in good yields. This domino method has been expanded for the synthesis of 2-acylbenzo[ b ]thiophenes using in situ generated iodine (I 2 ) from by-product KI in high yields. Treatment of xanthate with the copper( ii )-catalyst reduced it to a Cu( i )-catalyst, which initiates the catalytic cycle. A possible mechanism has been proposed based on the results from XPS-analysis, an iodine color test and several other control experiments. Efficient domino methods are developed for the synthesis of 2,3-dihydrobenzo[ b ]thiophenes and 2-acylbenzo[ b ]thiophenes from 2-iodoketones using in situ generated iodine from by-product KI with a Cu-catalyst and xanthate.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04647g