1,2,3-Triazole based ligands with phosphine and pyridine functionalities: synthesis, Pd^IIand Pt^IIchemistry and catalytic studies

Abstract

This manuscript describes the syntheses of pyridine appended triazole-based mono- and bisphosphines, [o-Ph2P(C6H4){1,2,3-N3C(Py)C(H)}] (2), [o-Br(C6H4){1,2,3-N3C(Py)C(PPh2)}] (3), [C6H5{1,2,3-N3C(Py)C(PPh2)}] (4), Ph2P(C6H4){1,2,3-N3C(Py)C(PPh2)}] (5) and [3-Ph2P-2-{1,2,3-N3C(Ph)C(PPh2)}C5H3N] (6), their palladium, platinum chemistry and catalytic applications....

Novel 1,2,3-triazolyl phosphine with a pyridyl functionality: synthesis, coinage metal complexes, photophysical studies and Cu(i) catalyzed C–O coupling of phenols with aryl bromides

“…Triazole derivative 2-(1-phenyl-1 H -1,2,3-triazole-4-yl)pyridine ( A ) was synthesized using a previously reported two-step synthetic procedure. 11 The lithiation of A followed by the addition of Ph 2 PCl resulted in a highly air stable 1,2,3-triazole functionalized tertiaryphosphine [2-{(C 6 H 4 N)(C 2 (PPh 2 )N 3 C 6 H 5 )}] ( 1 ) as shown in Scheme 1. 11 The 31 P{ 1 H} NMR spectrum of 1 showed a single resonance at −25.9 ppm and the high resolution mass spectrometry (HRMS) data showed a molecular ion peak at 407.1417 (calcd 407.1420) corresponding to [M + H] + .…”

“…[2-{(C 6 H 4 N)(C 2 (PPh 2 )N 3 C 6 H 5 )}] ( 1 ) was prepared according to the published procedures from our group. 11 CuCl, 30 CuBr 30 and [AuCl(SMe 2 )] 31 were prepared according to the published procedures or with slight modifications. Other regents and metal salts were purchased from Aldrich chemicals, and other local chemical suppliers and purified prior to use.…”

“…10 The electron rich triazole moiety along with the phosphine moiety on C-5 triazole carbon coordinated to the platinum metals proved to be an efficient system in catalytic transformations such as the α-alkylation reaction. 11 Thus, triazole-based phosphines with increased stability provide easier manipulation and also enhance reaction outcomes. 11,12 In this context, herein, we report the synthesis and group 11 metal chemistry of a triazolyl-phosphine with a pyridyl functionality [2-{(C 6 H 4 N)(C 2 (PPh 2 )N 3 C 6 H 5 )}] ( 1 ).…”

“…11 Thus, triazole-based phosphines with increased stability provide easier manipulation and also enhance reaction outcomes. 11,12 In this context, herein, we report the synthesis and group 11 metal chemistry of a triazolyl-phosphine with a pyridyl functionality [2-{(C 6 H 4 N)(C 2 (PPh 2 )N 3 C 6 H 5 )}] ( 1 ). Copper complexes have shown fluorescence behavior in the solid state due to the Cu⋯Cu interactions, which is supported by NBO analysis.…”

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

“…10 The presence of triazole and phosphine moieties in a ligand can complement increased stability, allow easier manipulation, and enhance the reaction outcomes. 11 Transition metal-catalyzed annulation processes have proven to be very useful in organic synthesis in the construction of a new ring on a molecule. 12 Indenones are important carbocyclic systems found in natural products and materials chemistry and find applications in pharmacology.…”