THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ENOL ACETATES OF ALPHA-BROMO KETONES WITH 1-ALKENYLBORON, ARYLBORON, OR ALKYLBORON COMPOUNDS - A FACILE SYNTHESIS OF KETONES AND THEIR ENOL ACETATES

被引：21

作者：

ABE, S ^{[1
]}

MIYAURA, N ^{[1
]}

SUZUKI, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV, FAC ENGN, DEPT APPL CHEM, SAPPORO, HOKKAIDO 060, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 10期

关键词：

D O I：

10.1246/bcsj.65.2863

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of stereodefined enol acetates of ketones is readily accomplished by palladium-catalyzed cross-coupling reaction between alkyl-, aryl-, or 1-alkenylboron reagents with enol acetates of alpha-bromo ketones. Hydroboration of alkene with 9-BBN, followed by coupling with (Z)-2-ethoxy-1-bromoethene gives the enol ether of aldehyde. These enol acetates and ethers are readily deprotected to give corresponding ketones and aldehydes in high yields.

引用

页码：2863 / 2865

页数：3

共 50 条

[21] Reversed-Polarity Synthesis of Diaryl Ketones via Palladium-Catalyzed Cross-Coupling of Acylsilanes
Schmink, Jason R.
Krska, Shane W.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) : 19574 - 19577
[22] Palladium-catalyzed carbonylative cross-coupling of organoboranes with hypervalent iodonium salts: Synthesis of aromatic ketones
Kang, SK
Lim, KH
Ho, PS
Yoon, SK
Son, HJ
SYNTHETIC COMMUNICATIONS, 1998, 28 (08) : 1481 - 1489
[23] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL IODIDES WITH ORGANOSTANNANES: SYNTHESIS OF UNSYMMETRICAL DIVINYL KETONES.
Goure, W.F.
Wright, Michael E.
Davis, P.D.
Labadie, Sharada S.
Stille, J.K.
Journal of the American Chemical Society, 1984, 106 (21): : 6417 - 6422
[24] Palladium-catalyzed carbonylative cross-coupling of organoboranes with hypervalent iodonium salts: Synthesis of aromatic ketones
Department of Chemistry, Sung Kyun Kwan University, Natural Science Campus, Suwon 440-746, Korea, Republic of
Synth. Commun., 8 (1481-1489):
[25] Access to Ketones through Palladium-Catalyzed Cross-Coupling of Phenol Derivatives with Nitroalkanes Followed by Nef Reaction
He, Xiaoyu
Hu, Sengui
Xiao, Yuxuan
Yu, Lin
Duan, Wengui
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (35)
[26] Fluoroalkylation of porphyrins: A facile synthesis of trifluoromethylated porphyrins by a palladium-catalyzed cross-coupling reaction
Liu, C
Chen, QY
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (17) : 3680 - 3686
[27] A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates
Ishiyama, T
Ahiko, T
Miyaura, N
TETRAHEDRON LETTERS, 1996, 37 (38) : 6889 - 6892
[28] An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones
Rao, Maddah L. N.
Venkatesh, Varadhachari
Jadhav, Deepak N.
TETRAHEDRON LETTERS, 2006, 47 (39) : 6975 - 6978
[29] Synthesis of Highly Functionalized Diaryl Ketones by Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Between Triarylbismuthines and Aryl(Heteroaryl) Iodides
Dansereau, Julien
Gautreau, Stephane
Gagnon, Alexandre
CHEMISTRYSELECT, 2017, 2 (08): : 2593 - 2599
[30] PALLADIUM-CATALYZED REACTION OF TRIBUTYLTIN HYDRIDE - REGIOSPECIFICALLY CONTROLLED FORMATION OF ALPHA-BROMO - ALPHA,ALPHA-DISUBSTITUTED KETONES FROM TRIBUTYLTIN BETA-KETOCARBOXYLATES
GUIBE, F
ZHANG, HX
BALAVOINE, G
NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1986, 10 (12): : 697 - 699

← 1 2 3 4 5 →