Bis(triphenylphosphine)palladium(II)succinimide as a precatalyst for Suzuki cross-coupling—subtle effects exerted by the succinimide ligand

Bis(triphenylphosphine)palladium(II)phthalimide – an easily prepared precatalyst for efficient Suzuki–Miyaura coupling of aryl bromides

“…The oxidative addition of succinimide to (Ph 3 P) 4 Pt and (Ph 3 P) 4 Pd, to give (Ph 3 P) 2 Pt(N-Succ)H and (Ph 3 P) 2 Pd(NSucc) 2 , respectively, has been investigated by Roundhill [41] and ourselves [42]. In analogous fashion, we have found that the readily available complex, (Ph 3 P) 4 Pd, reacted with two equivalents of phthalimide in benzene at 25 • C for 15 h to give the novel trans-complex 1 in 78% yield (Fig.…”

“…The following compounds characterized by 1 H, 13 C NMR spectroscopy and mass spectrometry are known within the literature: biphenyl 4a [52], 4-methylbiphenyl 4b [45], 4 -formylbiphenyl 4c [53], 4-chlorobiphenyl 4d [46] 4-acetylbiphenyl 4e [54], 4-acetyl-4 -methylbiphenyl 4f [55], 4-acetyl-4 -formylbiphenyl 4g [56], 4-acetyl-4 -chlorobiphenyl 4h [57], 4-nitrobiphenyl 4i [58], 4-nitro-4 -methylbiphenyl 4j [59], 4 -nitro-biphenyl-4-carbaldehyde 4k [60], 4-nitro-4 -chlorobiphenyl 4l [61], 2-methoxybiphenyl 4m [62], 3-(2-methoxyphenyl)thiophene 4n [63], 2-methoxy-trans-stilbene 4o [64], 2-methoxycarbonylbiphenyl 4p [65], 3-(2-methoxycarbonylphenyl)thiophene 4q [66], 2-methoxycarbonyl-trans-stilbene 4r [67], 2,6-dimethylbiphenyl 4s [68], 2,6-dimethyl-4 -methylbiphenyl 4t [42], 2,6-dimethyl-4 -formylbiphenyl 4u [42], 2,6-dimethyl-4 -chlorobiphenyl 4v [69], 4-bromo-6-methyl-2-pyrone 2h [48], 4-phenyl-6-methyl-2-pyrone 4w, 4-(4 -methylphenyl)-6-methyl-2-pyrone 4x [48], 4-(4 -formylphenyl)-6-methyl-2-pyrone 4y [48], 4-(4 -chlorophenyl)-6-methyl-2-pyrone 4z [48], 4-(2 -phenyl-trans-ethenyl)-6-methyl-2-pyrone 4ab [48]. …”

Pd‐Catalyzed Cycloisomerization of 4‐Aza‐1,6‐enynes to 3‐Aza‐bicyclo[4.1.0]hept‐2‐enes

“…To confirm this hypothesis, [Pd(mal) 2 (PPh 3 ) 2 ] was prepared according to a literature procedure [14] and used as the catalyst in the reaction. A test reaction of 1 a using this separately prepared catalyst under the same reaction conditions as in entry 4 in Table 1 afforded 1 c in 62 % yield (data not shown in Table 1), which is slightly higher than that produced using the [Pd(PPh 3 ) 4 ]/maleimide catalyst system (Table 1, entry 4, 51 % yield), indicating that [Pd(mal) 2 (PPh 3 ) 2 ] is the precursor of the active catalytic species.…”

“…[b] [Pd(C 4 H 2 NO 2 ) 2 (PPh 3 ) 2 ] was prepared according to the literature. [14] [c] When the reaction temperature was 110 8C, the yield of b and c were 0 and 62 %, respectively. Chem.…”

Synthesis and Characterization of a Cationic Phthalimido‐Functionalized N‐Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity

“…This concept has led us to explore a functionalized NHC ligand with an ancillary phthalimido unit. Imidate‐based Pd II bis(triphenylphosphine) complexes were found to be more active in C–C coupling reactions than (Ph 3 P) 2 PdCl 2 6. It is worth noting that imidate ligands [H 4 C 6 (CON – CO)] display coordination flexibility and multihapticity by coordination through their N and/or O atoms in a κ 2 coordination mode 7…”