Nickel-catalyzed coupling of aryl iodides with aromatic aldehydes: Chemoselective synthesis of ketones

被引：136

作者：

Huang, YC ^{[1
]}

Majumdar, KK ^{[1
]}

Cheng, CH ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 05期

关键词：

D O I：

10.1021/jo010289i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl iodides (ArI) couple with aryl aldehydes (Ar'CHO) in the presence of Ni(dppe)Br-2 and Zn to give the corresponding biaryl ketones (ArCOAr'). The use of a bidentate phosphine complex is critical to the success of this catalytic reaction. The reaction provides a new procedure for the synthesis of various functionalized biaryl ketones.

引用

页码：1682 / 1684

页数：3

共 23 条

[1] Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes
Bumagin, NA
Korolev, DN
[J]. TETRAHEDRON LETTERS, 1999, 40 (15) : 3057 - 3060
[2] FUNCTIONALIZED KETONES BY IRON MEDIATED REACTION OF GRIGNARD-REAGENTS WITH ACYL CHLORIDES
CARDELLICCHIO, C
FIANDANESE, V
MARCHESE, G
RONZINI, L
[J]. TETRAHEDRON LETTERS, 1987, 28 (18) : 2053 - 2056
[3] Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides
Feng, CC
Nandi, M
Sambaiah, T
Cheng, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) : 3538 - 3543
[4] A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids
Haddach, M
McCarthy, JR
[J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3109 - 3112
[5] Heitzler F. R., 1993, J ORG CHEM, V58, P2781
[6] OXIDATIVE NUCLEOPHILIC-ADDITION OF ORGANOVANADIUM REAGENTS TO ALDEHYDES WITH FORMATION OF KETONES
HIRAO, T
MISU, D
AGAWA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) : 7179 - 7181
[7] HUDLICKY M, 1989, ACS MONOGR SER, V186, P591
[8] Palladium-catalyzed carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles: Synthesis of biaryl ketones
Ishiyama, T
Kizaki, H
Hayashi, T
Suzuki, A
Miyaura, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) : 4726 - 4731
[9] SYNTHESIS OF UNSYMMETRICAL BIARYL KETONES VIA PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING REACTION OF ARYLBORONIC ACIDS WITH IODOARENES
ISHIYAMA, T
KIZAKI, H
MIYAURA, N
SUZUKI, A
[J]. TETRAHEDRON LETTERS, 1993, 34 (47) : 7595 - 7598
[10] A Heck-type reaction involving carbon-heteroatom double bonds.: Rhodium(I)-catalyzed coupling of aryl halides with N-pyrazyl aldimines
Ishiyama, T
Hartwig, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12043 - 12044

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