How to Choose pd(t-bu3p)2?

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Introduction

The catalyst bis(tri-tert-butylphosphine)palladium(0) [Pd(t-Bu3P)2, 1, CAS: 53199-31-8] is a colorless, air-sensitive solid that must be handled in a glove box or under inert gas. [Pd(t-Bu3P)2] (1) contains bulky, electron-rich tertiary phosphine ligands [t-Bu3P]. In palladium-catalyzed cross-coupling reactions, these ligands promote oxidative addition by stabilizing higher oxidation states. The bulky ligands also facilitate reductive elimination. Hence, 1 is superior in transition-metal-catalyzed cross-coupling reactions compared to the classical [Pd(Ph3P)4] catalyst. [Pd(t-Bu3P)2] efficiently performs typical cross-coupling reactions, including Stille, Negishi, Suzuki, Heck, Sonogashira, and Buchwald–Hartwig aminations, with electrophiles R-X (X = Cl, Br, I, OTf, SO2Cl, etc.). It is also effective for cross-coupling of organolithium reagents, alkenylgermanes, alkali-metal silanolates, and triorgano-indium reagents. Additionally, it has applications in arylation of hydrosiloxanes, decarboxylative cross-coupling, carbonylations and aminocarbonylations, carboiodinations, C-H functionalizations, cyanations, methylenation of olefins, and annulation reactions. Recently, 1 has become one of the leading new-generation catalysts, playing an essential role in organic synthesis.

[Pd(t-Bu3P)2] is commercially available but can also be prepared by treating [Pd(η5-C5H5)(η3-C3H5)] with the ligand [t-Bu3P] in n-hexane at room temperature for 3 hours. The pale red crude product can be recrystallized from n-hexane at –20 °C to yield pure colorless crystals.

Figure 1

tert

Table 1

The Use of Bis(tri-

tert

-butylphosphine)palladium(0) [Pd(

t

-Bu3P)2]

[Pd(t-Bu3P)2]-Catalyzed Cross-Coupling of Organolithium Reagents

Feringa and colleagues reported [Pd(t-Bu3P)2]-catalyzed cross-coupling reactions between alkyllithium reagents and a variety of aryl- and alkenylbromides under mild conditions. These cross-coupling reactions are highly selective, avoiding lithium–halogen exchange and homocoupling side reactions. The authors also extended the cross-coupling reactions to (hetero)aryllithium reagents using the in situ prepared catalyst [Pd2(dba)3] and [t-Bu3P] as ligands.

[Pd(t-Bu3P)2]-Catalyzed Cross-Coupling of Alkali-Metal Silanolates

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A broadly applicable protocol exists for the [Pd(t-Bu3P)2]-catalyzed cross-coupling of a wide range of alkali metal arylsilanolates with various aryl halides. This method also applies to the cross-coupling of heteroarylsilanolates.

[Pd(t-Bu3P)2]-Catalyzed Arylation of Hydrosiloxanes

Symmetrical and unsymmetrical siloxanes were synthesized by [Pd(t-Bu3P)2]-catalyzed arylation of hydrosiloxanes. This method was a one-pot process with high functional group tolerance and was also utilized to perform triple arylations.

[Pd(t-Bu3P)2]-Catalyzed Decarboxylative Cross-Coupling Reaction

Forgione and Biloudeau developed a highly selective Pd-catalyzed decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and various aryl halides in the presence of a reactive C-H group. This process provides a valuable alternative for other cross-coupling reactions when appropriate cross-coupling partners are not commercially available and are hard to synthesize.

[Pd(t-Bu3P)2]-Catalyzed Carbonylation and Aminocarbonylation

Traditional methods to synthesize acid chloride involve toxic reagents such as PCl3, thionyl chloride, and oxalyl chloride. Quesnel and Arndtsen described a new method to construct acid chlorides via the [Pd(t-Bu3P)2]-catalyzed carbonylation of aryl iodides under mild conditions. The decisive step of the process was the reductive elimination of [(t-Bu3P)(CO)Pd(COAr)Cl], facilitated by the combination of the bulky, electron-rich [t-Bu3P], the phosphine chloride, and CO coordination. This method was also exploited for traditional aminocarbonylation of aryl iodides under exceptionally mild conditions (ambient temperature and pressure).

[Pd(t-Bu3P)2]-Catalyzed Carboiodination

Various functionalized chromans and isochromans were prepared via the intramolecular [Pd(t-Bu3P)2]-catalyzed carboiodination of alkenyl aryl iodides in the presence of an amine base (Et3N). These cyclizations had a broad functional group tolerance and showed high diastereo-selectivities, originating from minimizing axial–axial interactions in the carbopalladation step.

[Pd(t-Bu3P)2]-Catalyzed C-H Functionalization

Tamba and colleagues described a facile [Pd(t-Bu3P)2]-catalyzed C-H arylation of heteroarene compounds with aryl bromides and aryl chlorides in the presence of LiOt-Bu as a base.

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