A Study of the Heck Reaction in Non-Polar Hydrocarbon Solvents and in Supercritical Carbon Dioxide

2007 ◽  
Vol 60 (8) ◽  
pp. 566 ◽  
Author(s):  
Jin-Kyun Lee ◽  
Rachel M. Williamson ◽  
Andrew B. Holmes ◽  
Edward J. Bush ◽  
Ian F. McConvey
Keyword(s):  
Butyl Acrylate ◽  
Heck Reaction ◽  
Supercritical Co2 ◽  
Phosphine Ligands ◽  
Triphenyl Phosphite ◽  
Heck Reactions ◽  
Polar Solvents ◽  
Phosphorus Ligands ◽  
Hydrocarbon Solvents ◽  
Sterically Demanding

The effects of electronic and steric properties of phosphorus ligands on Heck reactions in supercritical CO2 and non-polar hydrocarbon solvents were studied. In Heck reactions between iodobenzene and butyl acrylate, higher yields were obtained with less electron-rich phosphine ligands. This trend was also observed with the electron-poor triphenyl phosphite. A range of sterically demanding phosphites were then investigated. Biphenyl-containing phosphites 8 and 13 were found to be highly effective. In the Heck reaction between the less-reactive bromobenzene and butyl acrylate, the bulky, electron-rich tri-tert-butylphosphine ligand produced the best yield. These results emphasize the importance of both electronic and steric properties of phosphorus ligands in the Heck reaction in non-polar solvents.

Developing chiral phosphorus ligands for asymmetric hydrogenations

2010 ◽  
Vol 82 (7) ◽  
pp. 1429-1441 ◽  
Author(s):  
Wei Li ◽  
Guohua Hou ◽  
Xianfeng Sun ◽  
Gao Shang ◽  
Weicheng Zhang ◽  
...  
Keyword(s):  
Phosphine Ligands ◽  
Chiral Ligands ◽  
Phosphorus Ligands ◽  
Keto Esters ◽  
Asymmetric Hydrogenations ◽  
Dehydroamino Acid

Chiral rigid and electron-donating phosphocyclic phosphine ligands and modular atropisomeric biaryl phosphine ligands were designed and synthesized. The performance of these chiral ligands in the asymmetric hydrogenations of prochiral dehydroamino acid derivatives, enamides, imines, keto esters, and ketones has been demonstrated to be excellent.

Reductive Cross-Coupling of Vinyl Electrophiles

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3751-3763 ◽  
Author(s):  
Xing-Zhong Shu ◽  
Xiaobo Pang ◽  
Xuejing Peng
Keyword(s):  
Transition Metal ◽  
Heck Reaction ◽  
Structural Complexity ◽  
Cross Coupling ◽  
Heck Reactions ◽  
Promising Tool ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.1 Introduction2 Cross-Electrophile Coupling of Vinyl Electrophiles3 Reductive Heck Reaction of Vinyl Electrophiles4 Summary and Outlook

scholarly journals Complexes of the tripodal phosphine ligands PhSi(XPPh2)3(X = CH2, O): synthesis, structure and catalytic activity in the hydroboration of CO2

2016 ◽  
Vol 45 (37) ◽  
pp. 14774-14788 ◽  
Author(s):  
Alicia Aloisi ◽  
Jean-Claude Berthet ◽  
Caroline Genre ◽  
Pierre Thuéry ◽  
Thibault Cantat
Keyword(s):  
Catalytic Activity ◽  
Coordination Chemistry ◽  
Electronic Properties ◽  
Phosphine Ligands ◽  
Phosphorus Ligands ◽  
The Impact

The coordination chemistry of Fe2+, Co2+and Cu+ions was explored with the ligands PhSi{CH2PPh2}3(1) and PhSi{OPPh2}3(2), so as to evaluate the impact of the electronic properties of the tripodal phosphorus ligands on the structure and reactivity of the corresponding complexes.

Functional resins in palladium catalysis: promising materials for Heck reaction in aprotic polar solvents

2005 ◽  
Vol 234 (1) ◽  
pp. 1-13 ◽  
Author(s):  
A CAPORUSSO ◽  
P INNOCENTI ◽  
L ARONICA ◽  
G VITULLI ◽  
R GALLINA ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Palladium Catalysis ◽  
Polar Solvents

scholarly journals Tipping Point for Expansion of Layered Aluminosilicates in Weakly Polar Solvents: Supercritical CO2

2017 ◽  
Vol 9 (42) ◽  
pp. 36783-36791 ◽  
Author(s):  
Herbert T. Schaef ◽  
Narasimhan Loganathan ◽  
Geoffrey M. Bowers ◽  
R. James Kirkpatrick ◽  
A. Ozgur Yazaydin ◽  
...  
Keyword(s):  
Supercritical Co2 ◽  
Tipping Point ◽  
Polar Solvents

ChemInform Abstract: Phosphine Ligands. Part 7. 4,5-Bis(diphenylphosphino)acridine: A New Type of Tridentate Phosphorus-Nitrogen-Phosphorus Ligands.

ChemInform ◽  
2010 ◽  
Vol 29 (19) ◽  
pp. no-no
Author(s):  
S. HILLEBRAND ◽  
B. BARTKOWSKA ◽  
J. BRUCKMANN ◽  
C. KRUEGER ◽  
M. W. HAENEL
Keyword(s):  
Phosphine Ligands ◽  
Phosphorus Ligands ◽  
New Type ◽  
Nitrogen Phosphorus
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