A sequential highly stereoselective hydroboration and Suzuki-Miyaura cross-coupling reaction of fluoroalkylated internal acetylenes: a practical one-pot synthesis of fluoroalkylated trisubstituted alkenes

被引：40

作者：

Konno, T ^{[1
]}

Chae, J ^{[1
]}

Tanaka, T ^{[1
]}

Ishihara, T ^{[1
]}

Yamanaka, H ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 06期

关键词：

D O I：

10.1039/b316065c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The one-pot synthesis of trisubstituted alkenes starting from fluoroalkylated internal alkynes was investigated. Hydroboration of the alkynes proceeded in a highly regio- and stereoselective manner to give the corresponding vinylboranes in excellent yields. Without isolation, treatment of the vinylboranes with various aryl halides under the Suzuki-Miyaura cross-coupling conditions gave the fluoroalkylated trisubstituted alkenes in high yields with complete retention of the olefinic geometry.

引用

页码：690 / 691

页数：2

共 15 条

[1] ABRAHAM G, 1979, Patent No. 17853
[2] [Anonymous], 1990, DRUGS FUT, V15, P532
[3] Banks R. E., 1994, ORGANOFLUORINE CHEM
[4] A highly regio- and stereo-selective hydrostannation reaction of various fluorine-containing internal acetylene derivatives
Chae, JH
Konno, T
Kanda, M
Ishihara, T
Yamanaka, H
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 120 (02) : 185 - 193
[5] FILLER R, 1982, BIOCH ASPECTS FLUORI
[6] HYDROMETALLATION OF 1-ALKYL-3-TRIFLUOROMETHYL PROPARGYL ALCOHOLS
HANZAWA, Y
KAWAGOE, K
TANAHASHI, N
KOBAYASHI, Y
[J]. TETRAHEDRON LETTERS, 1984, 25 (42) : 4749 - 4752
[7] A facile synthesis of perfluoroalkyl vinyl iodides and their palladium-mediated cross-coupling reactions
Jennings, MP
Cork, EA
Ramachandran, PV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8763 - 8766
[8] Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
Konno, T
Chae, J
Kanda, M
Nagai, G
Tamura, K
Ishihara, T
Yamanaka, H
[J]. TETRAHEDRON, 2003, 59 (38) : 7571 - 7580
[9] KONNO T, IN PRESS ORG LETT
[10] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483

← 1 2 →