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Phosphine Ligands

A graphic representation of the chemical element Phosphorus from the periodic table, showing its atomic number ‘15’, and its atomic weight ‘30.973762’.

Phosphine ligands are the most significant class of ligands for cross-coupling because of the alterability of their electronic and steric properties. Ligands play a key role in stabilizing and activating the central metal atom and are used in reactions, such as transition metal catalyzed cross-coupling. Research has focused on the development of more effective ligands to improve catalyst performance. We offer an unprecedented portfolio of monodentate phosphine ligands and precursors, bidentate phosphine ligands and precursors, chiral ligands, Buchwald ligands, cataCXium® ligands, and DalPhos Ligands.   


Products

Buchwald-Hartwig Cross Coupling Reaction (164)

Suzuki-Miyaura Coupling (162)

Heck Reaction (147)

Negishi Coupling (146)

Sonogashira Coupling (146)

Stille Coupling (143)

phosphine (226)

aldehyde (2)

ligand (228)

catalyst (22)

polymerizable reagent (1)
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Triphenylphosphine
T84409

Triphenylphosphine

99%, ReagentPlus®

Trioctylphosphine
718165

Trioctylphosphine

97%, liquid

Xantphos
526460

Xantphos

97%

Trioctylphosphine oxide
223301

Trioctylphosphine oxide

99%, solid, ReagentPlus®

XPhos
638064

XPhos

98%

Diphenylphosphine
252964

Diphenylphosphine

98%, liquid

Tricyclohexylphosphine
261971

Tricyclohexylphosphine

solid

RuPhos
663131

RuPhos

98%, solid

Tri-<I>tert</I>-butylphosphine
570958

Tri-tert-butylphosphine

98%

Trioctylphosphine
117854

Trioctylphosphine

technical grade, 90%

BrettPhos
718742

BrettPhos

98%, solid

SPhos
638072

SPhos

98%

rac-BINAP
481084

rac-BINAP

97%

Tri(<I>o</I>-tolyl)phosphine
287822

Tri(o-tolyl)phosphine

97%

DPPF
177261

DPPF

97%, powder

cataCXium<SUP>®</SUP> A
671479

cataCXium® A

95%

<I>t</I>BuXPhos
638080

tBuXPhos

98%, solid

Tris(dimethylamino)phosphine
393290

Tris(dimethylamino)phosphine

97%, liquid

tBuBrettPhos
730998

tBuBrettPhos

97%, solid

Tributylphosphine
90827

Tributylphosphine

≥97% (Tri-N-butylphospine + isomers),≥93.5% (Tri-N-butylphosphine, GC), liquid


Monodentate Phosphine Ligands and Precursors

Monodentate phosphine ligands are compounds with only one phosphine atom available to interact with the metal. These ligands are not difficult to synthesize and allow for easy modifications. The flexibility of monophosphines allows for usage in reactions where certain activities or selectivities may be difficult to accomplish. We offer a wide variety of ligand motifs, including central chirality on the phosphorous atom, biaryl axial chirality, and planar chirality, to meet your research needs.

Bidentate Phosphine Ligands and Precursors

Bidentate phosphine ligands and precursors, also called diphosphines, are identified by the ligand having two phosphine atoms present connected by a side chain. Typically, this side chain is between two to four carbons long and forms an A-frame complex with the metal. Many bidenatate phoshine ligands and precursors have been designed to introduce a chiral ligand during synthesis. These ligands are very stable and able to form highly active and selective systems that allow for desired synthesis where other ligands have failed.

Buchwald Ligands

Buchwald ligands are bulky electron-rich dialkylbiaryl phospines and are known to improve reactivity in palladium catalysis. The structure of the ligand directly correlates to the efficiency of the catalysts contained in the ligand. The Buchwald group has continued to develop and modify these ligands, leading to the creation of ligands that are tailored to specific transformations.

cataCXium® Ligands

cataCXium® Ligands are highly effective ligands for palladium catalyzed cross-coupling reactions. Di-adamantylalkylphosphine, known as cataCXium® A, is a bulky and electron-rich phosphine ligand used for Heck and Suzuki couplings, Buchwald-Hartwig amination of arylchlorides, and α-arylation reactions of ketones. In reactions, these ligands allow for low catalyst loadings used under mild conditions. Recently, another class of basic, sterically-hindered phosphines featuring phosphino-substituted N-aryl pyrroles (cataCXium® P) has shown high catalyst turnover numbers for the Suzuki coupling of both electron-rich and electron-deficient aryl chlorides.

DalPhos Ligands

The bulky di(1-adamantyl)phosphino [P(1-Ad)2] fragment is common to the DalPhos ligand scaffold. These chelating N,P ligands are useful for Pd-catalyzed C–N and C–C bond formation. The more reactive Mor-DalPhos improves the scope and utility of ammonia coupling at room temperature and is also effective in coupling of hydrazine and acetone.




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