Suzuki–Miyaura Coupling Reactions of Fluorohalobenzenes

Synlett ◽  
2021 ◽  
Author(s):  
Peter Langer ◽  
Shoaib Iqbal ◽  
Muhammad Sharif
Keyword(s):  
Biological Research ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Organofluorine Compounds ◽  
Tremendous Impact

AbstractOrganofluorine compounds have gained interest in the fields of pharmaceuticals, agrochemicals, diagnostics, materials, and catalysis. Suzuki–Miyaura coupling reactions of fluorinated arenes made a tremendous impact in chemical and biological research and made organofluorinated molecules more readily available. This review gives a brief summary of Suzuki–Miyaura coupling reactions of fluorinated benzene derivatives. In this context, various aspects, such as regio­selectivity, efficiency, and applications, are discussed.1 Introduction2 Organofluorine Compounds3 Suzuki–Miyaura Reactions of Fluorohalobenzenes3.1 Fluorophthalates3.2 Reactions of Pentafluorohalobenzenes3.3 Tetrafluorohalobenzenes3.4 Trifluorohalobenzenes3.5 Difluorohalobenzenes3.6 Monofluorohalobenzenes3.7 Halo(trifluoromethyl)benzenes3.8 Trifluoromethyl Pyridines4 S Summary

Structure and Conformational Properties of three-layered Cyclophanes prepared by a one-pot Synthesis

2007 ◽  
Vol 2007 (7) ◽  
pp. 429-431
Author(s):  
Akihiko Tsuge ◽  
Takahiro Okamoto ◽  
Tetsuji Moriguch
Keyword(s):  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
Conformational Isomers ◽  
One Pot Synthesis ◽  
Conformational Properties

The coupling reactions of substituted bis(bromomethyl)benzene components and tetra(mercaptomethyl)benzene derivatives have been carried out under heterogeneous dilute reaction conditions to afford the three-layered cyclophanes 3a–e as three kinds of conformational isomers in moderate yields.

Synthesis of Benzamide Derivatives by the Reaction of Arenes and Isocyanides through a C–H Bond Activation Strategy

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 94-98 ◽  
Author(s):  
Mehdi Khalaj ◽  
Mahboubeh Taherkhani ◽  
Seyed Mousavi-Safavi ◽  
Jafar Akbari
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Benzamide Derivatives

A carbon–carbon bond formation reaction between isocyanides and benzene derivatives is reported. In contrast to traditional cross-coupling reactions, which require aryl halides or pseudohalides, we use a palladium catalyst to generate the aryl–palladium through C–H bond activation of arenes. This method offers an attractive approach to a range of benzamides from readily accessible benzene derivatives.

Nickel-catalyzed Suzuki–Miyaura type cross-coupling reactions of (2,2-difluorovinyl)benzene derivatives with arylboronic acids

2015 ◽  
Vol 13 (27) ◽  
pp. 7389-7392 ◽  
Author(s):  
Yang Xiong ◽  
Tao Huang ◽  
Xinfei Ji ◽  
Jingjing Wu ◽  
Song Cao
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

An unprecedented highly stereoselective example of nickel-catalyzed Suzuki–Miyaura type cross-coupling reactions of (2,2-difluorovinyl)benzene derivatives with arylboronic acids was developed.

Zirconocene-mediated selective synthesis of 1,4-bis(alkynyl)benzenes

2020 ◽  
Vol 44 (9-10) ◽  
pp. 571-575
Author(s):  
Bo Zhang ◽  
Hongmei Qu ◽  
Zhongxuan Li ◽  
Yuanyuan Zhai ◽  
Xiaolu Zhou ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Ester ◽  
Acid Ethyl Ester ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Phenylene Ethynylene ◽  
H Nmr ◽  
Vis Spectroscopy ◽  
High Yields ◽  
C Nmr

A series of novel 1,4-bis(alkynyl)benzene derivatives were synthesized from trimethylsilyl-substituted alkynes by the mediation of zirconocene with excellent regioselectivity in high yields. The 3,6-bis(trimethylsilyl)-4,5-dialkylphthalic acid dimethyl esters were prepared by cycloaddition of 2,5-bis(trimethylsilyl)zirconacyclopentadienes to dimethyl acetylenedicarboxylate. After iodination with iodine monochloride, 3,6-diiodo-4,5-dialkylphthalic acid dimethyl esters reacted with terminal alkynes to prepare the corresponding 1,4-bis(alkynyl)benzene derivatives by Sonogashira coupling reactions. After removal of trimethylsilyl, 4,5-dibutyl-3,6-bis(ethynyl)phthalic acid dimethyl ester (compound 3) reacted with 4-iodobenzoic acid ethyl ester and 2-iodothiophene, respectively, to obtain the corresponding products 4a and 4c. Compound 3 can be extended to higher oligomers, which reacted with 1-bromo-4-iodobenzene and phenylacetylene in a stepwise manner under Sonogashira conditions to give the phenylene-ethynylene oligomer 5 in an isolated yield of 85%. The structures of the products were confirmed by 1H NMR spectroscopy, 13C NMR spectroscopy, and MS. The optical properties of the 1,4-bis(alkynyl)benzene derivatives were studied by UV-Vis spectroscopy and fluorescence spectra. The results indicated that some can be developed into potential photovoltaic materials.

Time-Resolved Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light

2020 ◽  
Author(s):  
Rajdip Chowdhury ◽  
Zhunzhun Yu ◽  
Stefanie V. Kohlhepp ◽  
Xiang Yin ◽  
Abraham Mendoza
Keyword(s):  
Visible Light ◽  
Blue Light ◽  
Biological Systems ◽  
Biological Research ◽  
Coupling Reactions ◽  
Conceptual Basis ◽  
Time Resolved ◽  
Redox Active ◽  
Light Stimuli

<div><div><div><p>Flexible, small and strong alkyl ligations created upon external light stimuli can open new avenues for medicinal and biological research. Herein, we have found that NADH and analogues can drive photo-couplings without auxiliary photocatalysts. The time- resolved alkyl photo-ligation between redox-active carboxylate derivatives and electron-poor olefins displays a surprising moisture and air-tolerance, and unusually high coupling rates in dilute conditions. This work sets the conceptual basis for further biocompatible C-C coupling reactions promoted by visible-light in combination with NADH, the ubiquitous reductant of biological systems.</p></div></div></div>

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