Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

Yuanqiang Li; Michio Matsuda; Thies Thiemann; Tsuyoshi Sawada; Shuntaro Mataka; Masashi Tashiro

doi:10.1055/s-1996-5446

Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

Yuanqiang Li, Michio Matsuda, Thies Thiemann, Tsuyoshi Sawada, Shuntaro Mataka, Masashi Tashiro

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Thiophenes 1 have been treated with m-CPBA under BF₃·Et₂O catalysis. The thiophene-S-monoxides intermediary produced have been reacted in situ with various dienophiles. It could be shown that Lewis acid catalysis enhances the yield of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles can be used in the corresponding uncatalysed reaction. Thiophene-S-monoxides have also been isolated and subjected to subsequent cycloaddition in a two-step procedure.

Original language	English
Pages (from-to)	461-464
Number of pages	4
Journal	Synlett
Volume	1996
Issue number	5
DOIs	https://doi.org/10.1055/s-1996-5446
Publication status	Published - 1996
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-1996-5446

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title = "Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes",

abstract = "Thiophenes 1 have been treated with m-CPBA under BF3·Et2O catalysis. The thiophene-S-monoxides intermediary produced have been reacted in situ with various dienophiles. It could be shown that Lewis acid catalysis enhances the yield of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles can be used in the corresponding uncatalysed reaction. Thiophene-S-monoxides have also been isolated and subjected to subsequent cycloaddition in a two-step procedure.",

author = "Yuanqiang Li and Michio Matsuda and Thies Thiemann and Tsuyoshi Sawada and Shuntaro Mataka and Masashi Tashiro",

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AU - Li, Yuanqiang

AU - Matsuda, Michio

AU - Thiemann, Thies

AU - Sawada, Tsuyoshi

AU - Mataka, Shuntaro

AU - Tashiro, Masashi

PY - 1996

Y1 - 1996

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AB - Thiophenes 1 have been treated with m-CPBA under BF3·Et2O catalysis. The thiophene-S-monoxides intermediary produced have been reacted in situ with various dienophiles. It could be shown that Lewis acid catalysis enhances the yield of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles can be used in the corresponding uncatalysed reaction. Thiophene-S-monoxides have also been isolated and subjected to subsequent cycloaddition in a two-step procedure.

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JO - Synlett

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ER -

Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

Abstract

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