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

Access to Document

10.1055/s-1996-5446

Cite this

@article{8b786612449644fa938df3efe608ae13,

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",

year = "1996",

doi = "10.1055/s-1996-5446",

language = "English",

volume = "1996",

pages = "461--464",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "5",

}

TY - JOUR

T1 - Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

AU - Li, Yuanqiang

AU - Matsuda, Michio

AU - Thiemann, Thies

AU - Sawada, Tsuyoshi

AU - Mataka, Shuntaro

AU - Tashiro, Masashi

PY - 1996

Y1 - 1996

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/0007243634

UR - https://www.scopus.com/pages/publications/0007243634#tab=citedBy

U2 - 10.1055/s-1996-5446

DO - 10.1055/s-1996-5446

M3 - Article

AN - SCOPUS:0007243634

SN - 0936-5214

VL - 1996

SP - 461

EP - 464

JO - Synlett

JF - Synlett

IS - 5

ER -

Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this