Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions

2017 ◽  
Vol 53 (56) ◽  
pp. 7937-7940 ◽  
Author(s):  
Somsuvra Banerjee ◽  
Nitin T. Patil
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
Cross Coupling ◽  
Dual Role ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Polar Functional Groups ◽  
Transfer Agents

Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OH and B(OH)2.

Dual Role of Silanol Groups in Cyclopropanation and Hiyama−Denmark Cross-Coupling Reactions

2010 ◽  
Vol 12 (6) ◽  
pp. 1348-1351 ◽  
Author(s):  
Louis-Philippe B. Beaulieu ◽  
Lukas B. Delvos ◽  
André B. Charette
Keyword(s):  
Cross Coupling ◽  
Dual Role ◽  
Coupling Reactions ◽  
Silanol Groups ◽  
Cross Coupling Reactions

Efficient and recyclable Cu2(BDC)2(BPY)-catalyzed oxidative amidation of terminal alkynes: role of bipyridine ligand

2015 ◽  
Vol 5 (2) ◽  
pp. 851-859 ◽  
Author(s):  
Hanh T. N. Le ◽  
Thuan V. Tran ◽  
Nam T. S. Phan ◽  
Thanh Truong
Keyword(s):  
Efficient Method ◽  
Cross Coupling ◽  
Recyclable Catalyst ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Bipyridine Ligand ◽  
Oxidative Amidation

We have described an efficient method for oxidative cross coupling reactions between activated N–H amines and terminal alkynes using heterogeneous Cu2(BDC)2(BPY) as recyclable catalyst (BDC = benzene-1,4-dicarboxylate; BPY = 4,4′-bipyridine).

scholarly journals Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 565-573 ◽  
Author(s):  
Alasdair K. Cooper ◽  
Paul M. Burton ◽  
David J. Nelson
Keyword(s):  
Functional Groups ◽  
Density Functional ◽  
Aryl Halide ◽  
Cross Coupling ◽  
Density Functional Theory Calculations ◽  
Detailed Comparison ◽  
Coupling Reactions ◽  
Functional Theory ◽  
Cross Coupling Reactions

A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes
Keyword(s):  
Energy Transfer ◽  
Functional Groups ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
General Methodology ◽  
Cross Coupling Reactions ◽  
Electronically Excited ◽  
Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system

2012 ◽  
Vol 53 (28) ◽  
pp. 3556-3559 ◽  
Author(s):  
Marcio S. Silva ◽  
Renan S. Ferrarini ◽  
Bruno A. Sousa ◽  
Fabiano T. Toledo ◽  
João V. Comasseto ◽  
...  
Keyword(s):  
Catalytic System ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Oxidative C−H/C−H Cross-Coupling Reactions between N -Acylanilines and Benzamides Enabled by a Cp*-Free RhCl3 /TFA Catalytic System

2018 ◽  
Vol 130 (29) ◽  
pp. 9246-9250 ◽  
Author(s):  
Yang Shi ◽  
Luoqiang Zhang ◽  
Jingbo Lan ◽  
Min Zhang ◽  
Fulin Zhou ◽  
...  
Keyword(s):  
Catalytic System ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

The syntheses, structures and spectroelectrochemical properties of 6-oxo-verdazyl derivatives bearing surface anchoring groups

2022 ◽  
Author(s):  
Varshini Jayantha Kumar ◽  
Jian-Zhong Wu ◽  
Martyna Judd ◽  
Elodie ROUSSET ◽  
Marcus Korb ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Bearing Surface ◽  
Surface Anchoring ◽  
Verdazyl Radicals ◽  
Cross Coupling Reactions ◽  
Anchoring Groups ◽  
Spectroelectrochemical Properties

A series of 6-oxo verdazyl radicals functionalised at the 1- and 5-positions by methyl, thiomethyl and iodo groups were synthesised using conventional strategies. Facile Sonogashira cross-coupling reactions of terminal alkynes...

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