Conjugate Addition of Organoboron Compounds to α,β-Unsaturated Ketones Catalyzed by Nickelacycles

被引：0

作者：

Semba, Kazuhiko ^{[1
]}

Nagase, Kotaro ^{[1
]}

Nakao, Yoshiaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Kyoto 6158510, Japan

来源：

SYNLETT | 2023年 / 34卷 / 18期

关键词：

nickelacycles; nickel catalysis; organoboron compounds; enones; conjugate addition; AZA-CLAISEN REARRANGEMENT; ARYLBORONIC ACIDS; ASYMMETRIC 1,4-ADDITION; PALLADACYCLE CATALYSTS; OXABICYCLIC ALKENES; ALLYLIC AMINES; PALLADIUM; CARBONYL; ALDEHYDES; REAGENTS;

D O I：

10.1055/a-2150-2912

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic activity of nickelacycles in the conjugate addition of arylboronates to alpha,beta-unsaturated ketones was investigated. Nickelacycles afforded beta-arylated ketones in moderate to high yields, whereas an analogous palladacycle did not catalyze the reaction. Studies on the time course of the reaction confirmed that the nickelacycles act as active species in the conjugate addition reaction.

引用

页码：2227 / 2231

页数：5

共 46 条

[1] ELECTRONEGATIVITY VALUES FROM THERMOCHEMICAL DATA
ALLRED, AL
[J]. JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1961, 17 (3-4): : 215 - 221
[2] Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs
Anderson, CE
Donde, Y
Douglas, CJ
Overman, LE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) : 648 - 657
[3] Simple palladacyclic and platinacyclic catalysts for the 1,4-conjugate addition of arylboronic acids and arylsiloxanes to enones
Bedford, Robin B.
Betham, Michael
Charmant, Jonathan P. H.
Haddow, Mairi F.
Orpen, A. Guy
Pilarski, Lukasz T.
Coles, Simon J.
Hursthouse, Michael B.
[J]. ORGANOMETALLICS, 2007, 26 (25) : 6346 - 6353
[4] Catalytic Asymmetric Synthesis of Chiral Allylic Esters
Cannon, Jeffrey S.
Kirsch, Stefan F.
Overman, Larry E.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) : 15185 - 15191
[5] ccdc, 2268818 CCDC
[6] Cobalt(II)-Catalyzed 1,4-Addition of Organoboronic Acids to Activated Alkenes: An Application to Highly cis-Stereoselective Synthesis of Aminoindane Carboxylic Acid Derivatives
Chen, Min-Hsien
Mannathan, Subramaniyan
Lin, Pao-Shun
Cheng, Chien-Hong
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) : 14918 - 14922
[7] Ligand-Free Nickel-Catalysed 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds
Chen, Wen
Sun, Lu
Huang, Xi
Wang, Jiayi
Peng, Yanqing
Song, Gonghua
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (07) : 1474 - 1482
[8] C-C bond-forming reductive elimination of ketones, esters, and amides from isolated arylpalladium(II) enolates
Culkin, DA
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) : 5816 - 5817
[9] High enantioselection in the rearrangement of allylic imidates with ferrocenyl oxazoline catalysts
Donde, Y
Overman, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) : 2933 - 2934
[10] Dupont J., 2008, Palladacycles. Synthesis

← 1 2 3 4 5 →