AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo)benzene and benzyne

Asao Naoki; Kenichiro Sato

doi:10.1021/ol062268m

AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo)benzene and benzyne

Asao Naoki, Kenichiro Sato

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

77 Citations (Scopus)

Abstract

The AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic cyclization of o-alkynyl(oxo)benzenes.

Original language	English
Pages (from-to)	5361-5363
Number of pages	3
Journal	Organic letters
Volume	8
Issue number	23
DOIs	https://doi.org/10.1021/ol062268m
Publication status	Published - 2006 Nov 9

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic cyclization of o-alkynyl(oxo)benzenes.",

author = "Asao Naoki and Kenichiro Sato",

year = "2006",

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doi = "10.1021/ol062268m",

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journal = "Organic Letters",

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N2 - The AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic cyclization of o-alkynyl(oxo)benzenes.

AB - The AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic cyclization of o-alkynyl(oxo)benzenes.

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