51364-51-3 Usage
Description
Tris(dibenzylideneacetone) dipalladium (Tris DBA) is used as catalyst for a wide variety of Pd catalyzed reactions including Suzuki coupling, Heck coupling, Negishi coupling, Carroll reaarangement, Trost asymmetric allylic alkylation, Buchwald-Hartwig amination of acryl halides, fluorination of allylic chlorides, arylation of ketones, carbonylation of 1,1-dichloro-1-alkenes, ?-arylation of carboxylic esters, and conversion of aryl and vinyl triflates to aryl and vinyl halides. It is also involved in the synthesis of azepane. Tris DBA is also a novel inhibitor of N-myristoyltransferase-1 with significant antitumor activity.
Uses
Different sources of media describe the Uses of 51364-51-3 differently. You can refer to the following data:
1. Tris(dibenzylideneacetone)dipalladium is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors. Also used in the synthesis of polymer bulk-heterojunction solar sells as a semiconductor.
2. suzuki reaction
3. A cycloaddition catalyst.
Reactions
1. Catalyst precursor for conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.
2. Catalyst for the synthesis of epoxides.
3. Catalytic asymmetric allylic and homoallylic diamination of terminal olefins.
4. Site-selective benzylic sp3 palladium-catalyzed direct arylation.
5. Palladium-catalyzed one-pot synthesis of tricyclic indolines.
6. Active catalyst for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles.
7. Catalyst in combination with BINAP for the asymmetric Heck Arylation of olefins.
8. Precursor for palladium-catalyzed carbon-nitrigen bond formation.
9. Catalyst for α-arylation of ketones,
10. Cross-coupling of aryl halides with aryl boronic acids.
References
https://en.wikipedia.org/wiki/Tris(dibenzylideneacetone)dipalladium(0)
http://www.sigmaaldrich.com
https://www.alfa.com
https://pubchem.ncbi.nlm.nih.gov
S. S. Bhandarkar, J. Bromberg, C. Carrillo, P. Selvakumar, R. K. Sharma, B. N. Perry, B. Govindarajan, L. Fried, A. Sohn, K. Reddy and J. L. Arbiser, Tris (Dibenzylideneacetone) Dipalladium, a N-Myristoyltransferase-1 Inhibitor, Is Effective against Melanoma Growth In vitro and In vivo, Clinical Cancer Research, 2008, vol. 18, 5743-5748
Chemical Properties
dark purple solid
General Description
Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) participates in the synthesis of azepane. Crystal structure of Pd2(dba)3 has been determined by three-dimensional X-ray data. Crystals of Pd2(dba)3 are reported to crystalize in triclinic system. It is widely used Pd(0) source in Pd-mediated transformations.
Check Digit Verification of cas no
The CAS Registry Mumber 51364-51-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,3,6 and 4 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 51364-51:
(7*5)+(6*1)+(5*3)+(4*6)+(3*4)+(2*5)+(1*1)=103
103 % 10 = 3
So 51364-51-3 is a valid CAS Registry Number.
InChI:InChI=1/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b13-11+,14-12+;2*13-11-,14-12+;;
51364-51-3Relevant articles and documents
A Simply Synthesized, Tough Polyarylene with Transient Mechanochromic Response
Kempe, Fabian,Brügner, Oliver,Buchheit, Hannah,Momm, Sarah N.,Riehle, Felix,Hameury, Sophie,Walter, Michael,Sommer, Michael
, p. 997 - 1000 (2018)
A simple and high-yielding route to tough polyarylenes of the type poly(meta,meta,para-phenylene) (PmmpP) is developed. PmmpP is tough even in its as-synthesized state which has an intermediate molar mass of Mw≈60 kg mol?1 and exhibits outstanding mechanical properties at further optimized molecular weight of Mw=96 kg mol?1, E=0.9 GPa, ?=300 %. Statistical copolymers with para,para-spiropyran (SP) are mechanochromic, and the toughness allows mechanochromism to be investigated. Strained samples instantaneously lose color upon force release. DFT calculations show this phenomenon to be caused by the PmmpP matrix that allows build-up of sufficiently large forces to be transduced to SP, and the relatively unstable corresponding merocyanine (MC) form arising from the aromatic co-monomer. MC units covalently incorporated into PmmpP show a drastically reduced half life time of 3.1 s compared to 4.5 h obtained for SP derivatives with common 6-nitro substitution.
Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation
Vita, Maria Victoria,Caramenti, Paola,Waser, Jerome
supporting information, p. 5832 - 5835 (2015/12/11)
Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.
