Regioselective one-step synthesis of 4-fluoroalkylated isoquinolines via carbopalladation reaction of fluorine-containing alkynes

被引：45

作者：

Konno, T ^{[1
]}

Chae, JH ^{[1
]}

Miyabe, T ^{[1
]}

Ishihara, T ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 24期

关键词：

D O I：

10.1021/jo051700v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd-(PPh3)(4), the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer. No other regioisomer was detected.

引用

页码：10172 / 10174

页数：3

共 26 条

[1] PHOTOCHEMICAL TRIFLUOROMETHYLATION OF SOME AROMATIC AND HETEROAROMATIC-COMPOUNDS WITH TRIFLUOROMETHYL BROMIDE
AKIYAMA, T
KATO, K
KAJITANI, M
SAKAGUCHI, Y
NAKAMURA, J
HAYASHI, H
SUGIMORI, A
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) : 3531 - 3537
[2] [Anonymous], 1998, ISOQUINOLINE ALKALOI
[3] Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry
Brisdon, AK
Crossley, IR
[J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2420 - 2421
[4] ARYL TRIFLUOROMETHYL ACETYLENES
BUNCH, JE
BUMGARDNER, CL
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1987, 36 (03) : 313 - 317
[5] A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes
Chae, J
Konno, T
Ishihara, T
Yamanaka, H
[J]. CHEMISTRY LETTERS, 2004, 33 (03) : 314 - 315
[6] Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation
Croisy-Delcey, M
Croisy, A
Carrez, D
Huel, C
Chiaroni, A
Ducrot, P
Bisagni, E
Jin, L
Leclercq, G
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) : 2629 - 2641
[7] Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides
Dai, GX
Larock, RC
[J]. ORGANIC LETTERS, 2001, 3 (25) : 4035 - 4038
[8] GENSLER WJ, 1951, ORG REACTIONS, V6, P191
[9] CYCLOPALLADATED IMINES IN SYNTHESIS .2. A NEW SYNTHESIS OF ISOQUINOLINES
GIRLING, IR
WIDDOWSON, DA
[J]. TETRAHEDRON LETTERS, 1982, 23 (41) : 4281 - 4284
[10] GIRLING TR, 1988, J CHEM SOC P1, P1317

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