Synthesis of a class of binaphthyl monophosphine ligands with a naphthofuran skeleton and their applications in Suzuki–Miyaura coupling reactions

2018 ◽  
Vol 42 (8) ◽  
pp. 5967-5971 ◽  
Author(s):  
Zihong Zhou ◽  
Hao Liang ◽  
Wang Xia ◽  
Huixuan Chen ◽  
Yaqi Zhang ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Excellent Activity ◽  
Sterically Hindered

L6–Pd2(dba)3 showed excellent activity in the Suzuki–Miyaura reaction of sterically hindered and electron-rich aryl halides with aryl boronic acids.

scholarly journals Carbonylative Suzuki–Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives

2020 ◽  
Vol 18 (9) ◽  
pp. 1754-1759 ◽  
Author(s):  
Aya Ismael ◽  
Troels Skrydstrup ◽  
Annette Bayer
Keyword(s):  
Boronic Acid ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Aryl Bromides ◽  
Sterically Hindered

A new protocol for carbonylative coupling of sterically hindered aryl bromides with boronic acids featuring slow addition of the boronic acid as a strategy to suppress unwanted non-carbonylative couplings for sterically hindered aryl bromides.

Palladium-catalyzed cross-coupling reactions of aryl boronic acids with aryl halides in water

2009 ◽  
Vol 21 ◽  
pp. S124-S126 ◽  
Author(s):  
Shaoyan WANG ◽  
Zhiqiang ZHANG ◽  
Zhizhi HU ◽  
Yue WANG ◽  
Peng LEI ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

An efficient indenyl-derived phosphine ligand for the Suzuki–Miyaura coupling of sterically hindered aryl halides

2016 ◽  
Vol 14 (20) ◽  
pp. 4664-4668 ◽  
Author(s):  
Yan Liu ◽  
Hui Peng ◽  
Jia Yuan ◽  
Meng-Qi Yan ◽  
Xue Luo ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Phosphine Ligand ◽  
Aryl Halides ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Sterically Hindered

An air-stable aryl substituted indenyl phosphine used in combination with Pd(OAc)2 provides a highly efficient catalyst for the Suzuki–Miyaura cross-coupling reaction of sterically hindered aryl halides with aryl boronic acids.

Functionalized Pyrazoles as Agents in C–C Cross-Coupling Reactions

2014 ◽  
Vol 69 (1) ◽  
pp. 83-97 ◽  
Author(s):  
Marijana Pejic ◽  
Sebastian Popp ◽  
Michael Bolte ◽  
Matthias Wagner ◽  
Hans-Wolfram Lerner
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Second Step ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Suzuki Reactions ◽  
Microwave Assisted ◽  
Cross Coupling Reactions

The 1-tetrahydropyranyl-(THP-)protected pyrazoles 4-R-pz(THP) (R=pinacolatoboryl=Bpin (3a(THP)), Me3Si (4a(THP)), Me3Sn (5a(THP)), and 4-R-3,5-Ph2pz (R=Bpin (3b(THP)), Me3Si (4b(THP)), Me3Sn (5b(THP)) were obtained by the following syntheses: i) In a first step, 4-X-pz (X=Br (1a), I (2a)) and 4-X-3,5-Ph2pz (X=Br (1b), I (2b)) were reacted with 3,4-dihydro-2Hpyran (DHP) to give the related THP-protected bromo- or iodopyrazole derivatives. ii) In a second step these THP derivatives were metalated by treatment with nBuLi or iPrMgCl. Subsequent reactions of the THP-protected metallopyrazoles 4-M-pz(THP) and 4-M-3,5-Ph2pz(THP) (M=Li, MgBr) with Bpin(OiPr), Me3SiCl, and Me3SnCl yielded the pyrazole derivatives 3a(THP), 3b(THP), 4a(THP), 4b(THP), 5a(THP), and 5b(THP). In contrast to the stannylated pyrazoles 5a(THP) and 5b(THP), the corresponding borylated and silylated derivatives could be easily deprotected: treatment of 3a(THP), 3b(THP), and 4a(THP) with HCl yielded the parent pyrazoles 3a, 3b and 4a. The microwave-assisted C-C cross-coupling reactions of these pyrazoles with aryl halides were examined, e. g. Suzuki reactions of 3a with p-pentylphenylbromide, p-hexylphenylbromide, and p- (2-ethylhexyl)phenylbromide. Similar reactions were also performed with 1a, 1b, 2a, and 2b and aryl-substituted pinacolatoboranes or boronic acids. Crystals of 5b(THP) suitable for X-ray diffraction were grown (monoclinic P21/c) and their structure determined. The crystal structures of 1a·HBr (monoclinic P21/n), 1b (triclinic P̄1̄), (1c)2·HBr (monoclinic P2/c), 1c·HBr·(Br2)0.5 (triclinic P̄1̄), (2a)3·H2SO4 (triclinic P̄1̄), 3a (orthorhombic P212121), (3a)3·H2O (trigonal R3c), 3b (orthorhombic Pna21), and 4a (monoclinic Pc) reveal interesting hydrogen bonding networks.

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>

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

scholarly journals Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

ACS Omega ◽  
2021 ◽  
Author(s):  
Muhammad Asif Iqbal ◽  
Le Lu ◽  
Hina Mehmood ◽  
Ruimao Hua
Keyword(s):  
Direct Coupling ◽  
Aryl Halides ◽  
Coupling Reactions

The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines

Synlett ◽  
1999 ◽  
Vol 1999 (7) ◽  
pp. 1145-1147 ◽  
Author(s):  
Martina Havelková ◽  
Michal Hocek ◽  
Michal Česnek ◽  
Dalimil Dvořák
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions
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