Iridium-catalyzed reaction of aroyl chlorides with internal alkynes to produce substituted naphthalenes and anthracenes

被引：97

作者：

Yasukawa, T ^{[1
]}

Satoh, T ^{[1
]}

Miura, M ^{[1
]}

Nomura, M ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 43期

关键词：

D O I：

10.1021/ja0280269

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Benzoyl chlorides efficiently react with 2 equiv of dialkylacetylenes as well as diphenylacetylene in the presence of an iridium catalyst accompanied by decarbonylation to produce 1,2,3,4-tetrasubstituted naphthalenes in good yields. Use of 2-naphthoyl chlorides selectively affords the corresponding anthracene derivatives. Copyright © 2002 American Chemical Society.

引用

页码：12680 / 12681

页数：2

共 25 条

[1] REACTIONS OF TRANS-[IRCL(CO)(PPH3)2] AND TRANS-[RHCL(CO)(PPH3)2] WITH ORGANIC TETRAHALIDES - OXIDATIVE ADDITION AND FORMATION OF DIHALOALKENES
ALNAJJAR, IM
[J]. INORGANICA CHIMICA ACTA, 1987, 127 (02) : L47 - L48
[2] GENERATION OF (2,3-ETA)-NAPHTHALYNE-NICKEL(0) COMPLEXES AND THEIR REACTIONS WITH UNSATURATED MOLECULES
BENNETT, MA
HOCKLESS, DCR
WENGER, E
[J]. ORGANOMETALLICS, 1995, 14 (04) : 2091 - 2101
[3] DECARBONYLATION AND DEHYDROHALOGENATION OF ALIPHATIC ACYL HALIDES BY IRIDIUM AND RHODIUM COMPLEXES
BLUM, J
KRAUS, S
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 33 (02) : 227 - &
[4] A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes
Bowles, DM
Anthony, JE
[J]. ORGANIC LETTERS, 2000, 2 (01) : 85 - 87
[5] COMPLEXES OF THE PLATINUM METALS .30. FRAGMENTATION REACTIONS OF RHODIUM AND IRIDIUM TRICHLORO-ACETATES AND TRIBROMO-ACETATES
BOYAR, EB
ROBINSON, SD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (10): : 2113 - 2119
[6] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
Cho, JY
Tse, MK
Holmes, D
Maleczka, RE
Smith, MR
[J]. SCIENCE, 2002, 295 (5553) : 305 - 308
[7] Dietrich F, 1998, METAL CATALYZED CROS
[8] Harvey R.G., 1997, POLYCYCLIC AROMATIC
[9] PI-COMPLEXES OF THE TRANSITION METALS .10. ACETYLENIC PI-COMPLEXES OF CHROMIUM IN ORGANIC SYNTHESIS
HERWIG, W
METLESICS, W
ZEISS, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (23) : 6203 - 6207
[10] Rhodium-catalyzed reaction of aroyl chlorides with alkynes
Kokubo, K
Matsumasa, K
Miura, M
Nomura, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 6941 - 6946

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