321722-19-4

Basic information

• Product Name: [Pd(η-(C9H4(CH2C6H5)-1-Me2-2,3))(2,2'-bipyridine)]triflate
• CAS NO: 321722-19-4
• Molecular Weight: 645.01
• Mol File: 321722-19-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [Pd(η-(C9H4(CH2C6H5)-1-Me2-2,3))(2,2'-bipyridine)]triflate(CAS DataBase Reference)
• NIST Chemistry Reference: [Pd(η-(C9H4(CH2C6H5)-1-Me2-2,3))(2,2'-bipyridine)]triflate(321722-19-4)
• EPA Substance Registry System: [Pd(η-(C9H4(CH2C6H5)-1-Me2-2,3))(2,2'-bipyridine)]triflate(321722-19-4)

Safety Data

• Hazardous Substances Data: 321722-19-4(Hazardous Substances Data)

Upstream product

• 503-17-3 dimethylacetylene 
• 73491-36-8 thallium(I) triflate 

Relevant articles and documents

Palladium-assisted formation of carbon-carbon bonds. 9. Synthesis of (2-alkenylaryl)- and indenylpalladium complexes

(o-Formylaryl)palladium complexes [Pd{C6H(CHO)-6-R3-2,3,4}X(N-N)] [R = OMe; X = Cl; N-N = bpy (2,2′-bipyridine) (1a), tmeda (N,N,N′,N′-tetramethylethylenediamine) (1b). R = H; X = Br; N-N = bpy (2a), tmeda (2b)] react with ylides PhCHqqPPh3, pyCHqqPPh3 (py = 2-pyridyl), or ClCHqqPPh3 to give the (o-alkenylaryl)palladium derivatives [Pd{C6-HCHqqCHPh-6-(OMe)3-2,3,4}Cl(N-N)] [N-N = bpy (3a), N-N = tmeda (3b)], [Pd{C6HCHqqCHpy-6-(OMe)3-2,3,4}Cl(N-N)] [N-N = bpy (4)], [Pd{C6H(E-CHqqCHCl)-6-(OMe)3-2,3,4}-Cl(tmeda)] (5), or [Pd(C6H4CHqqCHPh-2)Br(N-N)] [N-N = bpy (6a), N-N = tmeda (6b)]. The compounds 3a, 4, and 6a,b are obtained as mixtures of E and Z isomers, whereas the formation of 3b and 5 is stereoselective (E isomer). The reaction of the (o-acetylaryl)palladium complexes [Pd{C6HC(O)Me-6-(OMe)3-2,3,4}Cl(tmeda)] (7) and [Pd{C6H4(C(O)Me)-2}Br(bpy)] (8) with bases results in the formation of the 3-palladaindan-1-ones [Pd(κ2-{C6HC(O)CH2-6-(OMe)3-2, 3,4})(tmeda)] (9) and [Pd(κ2-{C6H4C(O)CH2-2}(bpy)] (10). Complexes 3b and 6a,b react with alkynes RCqqCR′ to give indenylpalladium complexes [Pd{η-C9HBn-1-R-2-R′-3-(OMe)3-5, 6,7}(tmeda)]TfO [Bn = benzyl, TfO = CF3SO3, R = R′ = Me (11); R = C(O)Me, R′ = H (12)] and [Pd{η-C9H4Bn-1-R-2-R′-3}(N-N)]TfO [R = R′ = H, N-N = bpy (13a), tmeda (13b); R = R′ = Me, N-N = bpy (14a), tmeda (14b); R = R′ = Et, N-N = bpy (15a), tmeda (15b); R = R′ = Ph, N-N = bpy (16a), tmeda (16b); R = Ph, R′ = H and R = H, R′ = Ph, N-N = bpy (17a); R = H, R′ = Ph, N-N = tmeda (17b); R = Ph, R′ = Me, N-N = bpy (18a), N-N = tmeda (18b)]. Complex 3b reacts with Me2CqqCqqCH2, CS2, or MeNqqCqqS to give [Pd(η3-CMe2C{C6H(E-CHqqCHPh)- 6-(OMe)3-2,3,4}CH2)(tmeda)]TfO (19), [Pd(S2C{C6H-(E-CHqqCHPh)-6-(OMe)3-2,3,4}) (tmeda)]TfO (20), or [Pd(SC(NMe){C6H(E-CHqqCHPh)-6-(OMe)3-2,3,4}) (tmeda)]TfO (21). The crystal structures of 12, 17b, and 18a have been determined; the hapticities of the indenyl five-membered rings are intermediate between η3 and η5.