Preparations of Saturated N-P-N Type Secondary Phosphine Oxides and their Applications in Cross-Coupling Reactions

2016 ◽  
Vol 63 (4) ◽  
pp. 353-367 ◽  
Author(s):  
Yu-Chang Chang ◽  
Ya-Han Liang ◽  
Fung-E Hong
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Cross Coupling Reactions

Heteroatom-substituted secondary phosphine oxides for Suzuki-Miyaura cross-coupling reactions

2016 ◽  
Vol 808 ◽  
pp. 23-33 ◽  
Author(s):  
Yu-Chang Chang ◽  
Yi-Chang Lee ◽  
Meng-Fan Chang ◽  
Fung-E. Hong
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Cross Coupling Reactions

A diphenyl ether derived bidentate secondary phosphine oxide as a preligand for nickel-catalyzed C–S cross-coupling reactions

2015 ◽  
Vol 13 (44) ◽  
pp. 10802-10807 ◽  
Author(s):  
Nadeesha P. N. Wellala ◽  
Hairong Guan
Keyword(s):  
Phosphine Oxide ◽  
Diphenyl Ether ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

A bidentate secondary phosphine oxide is a more effective preligand than Ph2P(O)H in nickel-catalyzed C–S cross-coupling reactions.

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

2006 ◽  
Vol 78 (2) ◽  
pp. 209-214 ◽  
Author(s):  
Lutz Ackermann ◽  
Robert Born ◽  
Julia H. Spatz ◽  
Andreas Althammer ◽  
Christian J. Gschrei
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Aryl Chlorides ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Studies on the use of easily accessible heteroatom-substituted secondary phosphine oxides as preligands for cross-coupling reactions are described. These air-stable sterically hindered phosphine oxides allow for efficient palladium-catalyzed Suzuki- and nickel-catalyzed Kumada-coupling reactions using electronically deactivated aryl chlorides. In addition, they enable nickel-catalyzed coupling reactions of magnesium organyls with aryl fluorides at ambient temperature, and ruthenium-catalyzed coupling reactions of aryl chlorides via C-H bond activation. Finally, the application of modular diamino phosphine chlorides as preligands for a variety of transition-metal-catalyzed C-C and C-N bond formation reactions employing electron-rich aryl chlorides is presented.

Rational design of novel ligands for environmentally benign cross-coupling reactions

2011 ◽  
Vol 83 (3) ◽  
pp. 633-644 ◽  
Author(s):  
Oleg M. Demchuk ◽  
Katarzyna Kielar ◽  
K. Michał Pietrusiewicz
Keyword(s):  
Rational Design ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Environmentally Benign ◽  
Rhodium Complexes ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Bismuth Triflate

Transition-metal (TM) complexes of new phosphines, readily prepared by a straight-forward three-step modular synthesis, were successfully employed in difficult cross-coupling reactions conducted under mild conditions (water, “open-flask”, low temperature) that aspire to meet green chemistry criteria. High yielding catalyzed by bismuth or rhodium complexes oxidative arylation of naphthoquinone gave the key 2-arylnaphthoquinone intermediates for facile bismuth triflate-catalyzed Michael addition of secondary phosphine oxides. Subsequent O-methylation and reductions of the resulting products gave access to the target air-stable phosphine ligands in good overall yields (up to 60 %).

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