S(IV)–Mediated Unsymmetrical Heterocycle Cross-Couplings

2019 ◽  
Author(s):  
Min Zhou ◽  
Jet Tsien ◽  
Tian Qin
Keyword(s):  
Cross Coupling ◽  
Reductive Elimination ◽  
Facile Synthesis ◽  
Trigonal Bipyramidal

<p>Herein we report a sulfur (IV) mediated cross-coupling for facile synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles onto a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion. <br></p>

S(IV)–Mediated Unsymmetrical Heterocycle Cross-Couplings

2019 ◽  
Author(s):  
Min Zhou ◽  
Jet Tsien ◽  
Tian Qin
Keyword(s):  
Cross Coupling ◽  
Reductive Elimination ◽  
Facile Synthesis ◽  
Trigonal Bipyramidal

<p>Herein we report a sulfur (IV) mediated cross-coupling for facile synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles onto a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion. <br></p>

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>

Suzuki-Miyaura cross-coupling reaction in water: facile synthesis of (hetero) aryl uracil bases using potassiumorganotrifluoroborates under microwave irradiation.

2016 ◽  
Vol 1 (15) ◽  
pp. 4721-4725 ◽  
Author(s):  
Bhaskaran Savitha ◽  
Ayyiliath M. Sajith ◽  
Eeda Koti Reddy ◽  
C. S. Ananda Kumar ◽  
M. Syed Ali Padusha
Keyword(s):  
Microwave Irradiation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Facile Synthesis ◽  
Cross Coupling Reaction ◽  
Reaction In Water

Ni(COD)(DMFU): A Heteroleptic 16-Electron Precatalyst for 1,2-Diarylation of Alkenes

Synlett ◽  
2021 ◽  
Author(s):  
Nana Kim ◽  
Van T. Tran ◽  
Omar Apolinar ◽  
Steven Wisniewski ◽  
Martin Eastgate ◽  
...  
Keyword(s):  
Nickel Complex ◽  
Active Catalyst ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Beneficial Effects ◽  
Cross Coupling Reactions ◽  
Growing Body ◽  
Hydride Elimination

Electron-deficient olefin (EDO) ligands are known to promote a variety of nickel-catalyzed cross-coupling reactions, presumably by accelerating the reductive elimination step and preventing undesired β-hydride elimination. While there is a growing body of experimental and computational evidence elucidating the beneficial effects of EDO ligands, significant gaps remain in our understanding of the underlying coordination chemistry of the Ni–EDO species involved. In particular, most procedures rely on in situ assembly of the active catalyst, and there is a paucity of pre-ligated Ni-EDO precatalysts. Herein, we investigate the 16-electron, heteroleptic nickel complex, Ni(COD)(DMFU), and examine the performance of this complex as a precatalyst in 1,2-diarylation of alkenes.

Novel and facile synthesis of 1-benzazepines via copper-catalyzed oxidative C(sp3)–H/C(sp2)–H cross-coupling

2017 ◽  
Vol 53 (90) ◽  
pp. 12229-12232 ◽  
Author(s):  
Rui Wang ◽  
Ruo-Xing Jin ◽  
Zi-Yang Qin ◽  
Kang-Jie Bian ◽  
Xi-Sheng Wang
Keyword(s):  
Cross Coupling ◽  
Facile Synthesis ◽  
Synthetic Strategy

A novel synthetic strategy for the facile construction of 1-benzazepines has been developedviacopper-catalyzed oxidative C(sp3)–H/C(sp2)–H cross-coupling.

A Facile Synthesis of Perfluoroalkyl Vinyl Iodides and Their Palladium-Mediated Cross-Coupling Reactions1

2000 ◽  
Vol 65 (25) ◽  
pp. 8763-8766 ◽  
Author(s):  
Michael P. Jennings ◽  
Elizabeth A. Cork ◽  
P. Veeraraghavan Ramachandran
Keyword(s):  
Cross Coupling ◽  
Facile Synthesis ◽  
Vinyl Iodides

scholarly journals DFT Study of Unstrained Ketone C-C Bond Activation via Rhodium(I)-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Dengmengfei Xiao ◽  
Lili Zhao ◽  
Diego Andrada
Keyword(s):  
Density Functional ◽  
Bond Activation ◽  
Chemical Reactivity ◽  
Cross Coupling ◽  
Underlying Mechanism ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Co Catalysts ◽  
Cross Coupling Reactions ◽  
Strain Model

Unstrained cyclic ketones can participate in cooperative Suzuki-Miyaura cross-coupling type reaction using rhodium(I)-based catalyst via C-C bond activation. The regioselectivity indicates a trend where the most substituted side is activated and it is controlled by the beta-substituents. In this work, Density Functional Theory (DFT) calculations have been carried out to disclose the underlying mechanism in the reaction of a ketone series and arylboronate using ylidene as ancillary ligand and pyridine as co-catalysts. The computed energies suggest the reductive elimination step with the highest energy while the reductive elimination has the highest energy barrier. By the means of the Activation Strain Model (ASM) of chemical reactivity, it is found that the ketone strain energy released on the oxidative addition does not control the relativity of the OA reactivity, but indeed is the interaction energy between Rh(I) and C-C bond the ruling effect. The effect of the beta-substituents on regioselectivity has been additionally studied.

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