Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands:  A Kinetic, Computational, and Synthetic Investigation

2007 ◽  
Vol 129 (43) ◽  
pp. 13001-13007 ◽  
Author(s):  
Takashi Ikawa ◽  
Timothy E. Barder ◽  
Mark R. Biscoe ◽  
Stephen L. Buchwald
Keyword(s):  
Phosphine Ligands ◽  
Aryl Chlorides ◽  
Synthetic Investigation

Easily Accessible and Highly Tunable Indolyl Phosphine Ligands for Suzuki−Miyaura Coupling of Aryl Chlorides

2007 ◽  
Vol 9 (15) ◽  
pp. 2795-2798 ◽  
Author(s):  
Chau Ming So ◽  
Chak Po Lau ◽  
Fuk Yee Kwong
Keyword(s):  
Phosphine Ligands ◽  
Aryl Chlorides

A Highly Efficient Ruthenium(II) Catalyst with (1,2-Diarylvinyl)phosphine Ligands for Direct OrthoArylation of 2-Arylpyridine with Aryl Chlorides

2010 ◽  
Vol 29 (14) ◽  
pp. 3222-3226 ◽  
Author(s):  
Bingran Yu ◽  
Xiaoyu Yan ◽  
Song Wang ◽  
Ning Tang ◽  
Chanjuan Xi
Keyword(s):  
Phosphine Ligands ◽  
Aryl Chlorides ◽  
Highly Efficient

P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

2012 ◽  
Vol 53 (29) ◽  
pp. 3754-3757 ◽  
Author(s):  
Shun Man Wong ◽  
Chau Ming So ◽  
Kin Ho Chung ◽  
Chi Him Luk ◽  
Chak Po Lau ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Phosphine Ligands ◽  
Aryl Chlorides ◽  
Palladium Catalyzed

ChemInform Abstract: P,N-Type Benzimidazolyl Phosphine Ligands for the Palladium-Catalyzed Suzuki Coupling of Potassium Aryltrifluoroborates and Aryl Chlorides.

ChemInform ◽  
2012 ◽  
Vol 43 (42) ◽  
pp. no-no
Author(s):  
Shun Man Wong ◽  
Chau Ming So ◽  
Kin Ho Chung ◽  
Chi Him Luk ◽  
Chak Po Lau ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Phosphine Ligands ◽  
Aryl Chlorides ◽  
Palladium Catalyzed

scholarly journals Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization

Science ◽  
2018 ◽  
Vol 362 (6415) ◽  
pp. 670-674 ◽  
Author(s):  
Shibin Zhao ◽  
Tobias Gensch ◽  
Benjamin Murray ◽  
Zachary L. Niemeyer ◽  
Matthew S. Sigman ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Three Dimensional ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Dimensional Structure ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Synthetic Investigation ◽  
Absolute Stereochemistry ◽  
Ligand Parameterization

Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed.

scholarly journals Palladium(II)-catalyzed Suzuki–Miyaura Reactions of Arylboronic Acid with Aryl Halide in the Presence of Aryl-Ferrocenyl-Phosphines

2013 ◽  
Vol 16 (1) ◽  
pp. 79
Author(s):  
A.T. Khabiyev ◽  
B.S. Selenova
Keyword(s):  
Catalytic Activity ◽  
Phenylboronic Acid ◽  
Potassium Phosphate ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Weak Base ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions

<p>This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extreme This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, also for reactions of aryl chlorides by temperature 100 ºC and pressure 1 atm. Sterically demanding and strongly Lewis-basic ferrocene-based phosphines are water- and oxygen-resistant. The Suzuki–Miyaura reaction is also an important reaction in the ground and fine organic synthesis, in the production of drugs and intermediates. To analyze the conversion of halogen aryl compounds the <sup>1</sup>H NMR spectroscopy was used. The advantage of Suzuki–Miyaura reaction in comparison with other cross-coupling reactions (Kumada-, Heck-, Heck-Carbonylation-, Murahashi-, Sonogashira-, Negishi-, Stille-reaktion, etc.) is in the usage of low toxic, water- and oxygen-insensitive thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. Catalyst, precursor and weak base were dissolved in toluene. All reactions were performed under an atmosphere of nitrogen or argon. The catalytic cycle of Suzuki–Miyaura reaction typically includes three main steps: oxidative addition of the haloaromatic to catalytic active palladium (0) species, transmetalation, and reductive elimination of the product under back formation of catalytically active species. All used catalysts showed good activity with aryl bromides and weak activity with aryl chlorides.</p>

scholarly journals Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide‐Functionalized Phosphine Ligands

2021 ◽  
Author(s):  
Zhiyong Hu ◽  
Xiao‐Jing Wei ◽  
Jens Handelmann ◽  
Ann‐Katrin Seitz ◽  
Ilja Rodstein ◽  
...  
Keyword(s):  
Phosphine Ligands ◽  
Aryl Chlorides

Nickel(II) Complexes of Bidentate N-Heterocyclic Carbene/Phosphine Ligands: Efficient Catalysts for Suzuki Coupling of Aryl Chlorides

2007 ◽  
Vol 13 (2) ◽  
pp. 582-591 ◽  
Author(s):  
Chun-Chin Lee ◽  
Wei-Chi Ke ◽  
Kai-Ting Chan ◽  
Chun-Liang Lai ◽  
Ching-Han Hu ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Phosphine Ligands ◽  
Aryl Chlorides
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