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

78 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

Access to Document

10.1021/ol062268m

Cite this

@article{c0716cd58bf24e90b892d1e15f060f49,

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

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",

month = nov,

day = "9",

doi = "10.1021/ol062268m",

language = "English",

volume = "8",

pages = "5361--5363",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo)benzene and benzyne

AU - Naoki, Asao

AU - Sato, Kenichiro

PY - 2006/11/9

Y1 - 2006/11/9

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.

UR - http://www.scopus.com/inward/record.url?scp=33845275322&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845275322&partnerID=8YFLogxK

U2 - 10.1021/ol062268m

DO - 10.1021/ol062268m

M3 - Article

C2 - 17078718

AN - SCOPUS:33845275322

VL - 8

SP - 5361

EP - 5363

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 23

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this