Kinetic Studies of the Oxidative Addition and Transmetallation Steps Involved in the Cross-Coupling of Alkynyl Stannanes with Aryl Iodides Catalysed byη2-(Dimethyl fumarate)(iminophosphane)palladium(0) Complexes

2004 ◽  
Vol 2004 (4) ◽  
pp. 732-742 ◽  
Author(s):  
Bruno Crociani ◽  
Simonetta Antonaroli ◽  
Luciano Canovese ◽  
Paolo Uguagliati ◽  
Fabiano Visentin
Keyword(s):  
Oxidative Addition ◽  
Cross Coupling ◽  
Kinetic Studies ◽  
Dimethyl Fumarate ◽  
Aryl Iodides ◽  
The Cross

Mechanistic study on the cross-coupling of alkynyl stannanes with aryl iodides catalyzed by η2-(dimethyl fumarate)palladium(0) complexes with iminophosphine ligands

2003 ◽  
pp. 2194-2202 ◽  
Author(s):  
Bruno Crociani ◽  
Simonetta Antonaroli ◽  
Valentina Beghetto ◽  
Ugo Matteoli ◽  
Alberto Scrivanti
Keyword(s):  
Cross Coupling ◽  
Dimethyl Fumarate ◽  
Mechanistic Study ◽  
Aryl Iodides ◽  
The Cross

Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (111) ◽  
pp. 109296-109300 ◽  
Author(s):  
Xian Wang ◽  
Zhenhua Wang ◽  
Zunyuan Xie ◽  
Guofang Zhang ◽  
Weiqiang Zhang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
The Cross

1,3-Yones as σ-, π-electron donating ligands significantly accelerated the cross-coupling reactions of aryl iodides with terminal alkynes, in which as low as 0.1 to 1 mol% of CuI were efficiently activated.

Aldehydes and Ketones Influence Reactivity and Selectivity in Nickel-Catalyzed Suzuki-Miyaura Reactions

2019 ◽  
Author(s):  
Alasdair Cooper ◽  
David Leonard ◽  
Sonia Bajo ◽  
Paul Burton ◽  
David Nelson
Keyword(s):  
Carbonyl Group ◽  
Functional Groups ◽  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cross Coupling Reaction ◽  
Site Selectivity ◽  
Aldehydes And Ketones ◽  
The Cross

We show that the energetically-favorable coordination of aldehydes and ketones – but not esters – to nickel(0) during Suzuki-Miyaura reactions can lead either to exquisite selectivity and enhanced reactivity, or to the inhibition<br>of the reaction. Aryl halides where the C-X bond is connected to the same π-system as an aldehyde or ketone functional<br>group undergo unexpectedly rapid oxidative addition, and are selectively cross-coupled during inter- and intramolecular<br>competition reactions. When aldehydes and ketones are present elsewhere, such as in the form of exogenous additives,<br>the cross-coupling reaction is inhibited depending on how strongly the pendant carbonyl group can coordinate to nickel(0). This work advances our understanding of how common functional groups interact with nickel(0) catalysts, and presents synthetic chemists with a tool that can be used to achieve site-selectivity in functionalized molecules. <br>

scholarly journals Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

2017 ◽  
Vol 13 ◽  
pp. 2122-2127 ◽  
Author(s):  
James R Vyvyan ◽  
Courtney A Engles ◽  
Scott L Bray ◽  
Erik D Wold ◽  
Christopher L Porter ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cyclic Ether ◽  
Carbon Skeleton ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
Type Coupling ◽  
The Cross

Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald–Hartwig etherification. The cyclic ether produced contains the carbon skeleton of heliannuol A.

Aldehydes and Ketones Influence Reactivity and Selectivity in Nickel-Catalyzed Suzuki-Miyaura Reactions

2019 ◽  
Author(s):  
Alasdair Cooper ◽  
David Leonard ◽  
Sonia Bajo ◽  
Paul Burton ◽  
David Nelson
Keyword(s):  
Carbonyl Group ◽  
Functional Groups ◽  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cross Coupling Reaction ◽  
Site Selectivity ◽  
Aldehydes And Ketones ◽  
The Cross

We show that the energetically-favorable coordination of aldehydes and ketones – but not esters – to nickel(0) during Suzuki-Miyaura reactions can lead either to exquisite selectivity and enhanced reactivity, or to the inhibition<br>of the reaction. Aryl halides where the C-X bond is connected to the same π-system as an aldehyde or ketone functional<br>group undergo unexpectedly rapid oxidative addition, and are selectively cross-coupled during inter- and intramolecular<br>competition reactions. When aldehydes and ketones are present elsewhere, such as in the form of exogenous additives,<br>the cross-coupling reaction is inhibited depending on how strongly the pendant carbonyl group can coordinate to nickel(0). This work advances our understanding of how common functional groups interact with nickel(0) catalysts, and presents synthetic chemists with a tool that can be used to achieve site-selectivity in functionalized molecules. <br>

Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides

2018 ◽  
Vol 20 (3) ◽  
pp. 760-763 ◽  
Author(s):  
Nai-Wei Liu ◽  
Kamil Hofman ◽  
André Herbert ◽  
Georg Manolikakes
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Sulfinic Acid ◽  
Aryl Iodides ◽  
The Cross ◽  
Dual Catalysis ◽  
Acid Salts

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

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