The iminophosphine 2-(2-Ph2P)C6H4N=CHC6H4OH (P-N-OH) reacts with [Pd(m-Cl)(h3-C3H5)]2 yielding [PdCl(P-N-O)] and propene. In the presence of NEt3, the reaction of P-N-OH with [Pd(m-Cl)(h3-1-R1,3-R2C3H3)]2 (R1 = R2 = H, Ph; R1 = H, R2 = Ph) affords the h1-allyl derivatives [Pd(h1-1-R1,3-R2C3H3)](P-N-O)] (R1 = R2 = H: 1; R1 = H, R2 = Ph: 2; R1 = R2 = Ph: 3). In solution, the complexes 1 and 3 undergo a slow dynamic process which interconverts the bonding site of the allyl ligand. The X-ray structural analysis of 1 indicates a square-planar coordination geometry around the palladium centre with a P,N,O,-tridentate ligand and a s bonded allyl group. The complexes [PdR(P-N-O)] (R = C6H4Me-4, C≡CPh) react slowly with p-bromoanisole in the presence of p-tolylboronic acid to give [PdBr(P-N-O)] and the coupling product RC6H4OMe-4. The latter reactions also proceed at a low rate under catalytic conditions. The coupling of allyl bromide with p-tolylboronic acid is catalyzed by [PdCl(P-N-O)]/K2CO3 to give 4-allyltoluene.

Palladium complexes with a tridentate PNO ligand. Synthesis of eta 1-allyl complexes and cross-coupling reactions promoted by boron compounds / B. Crociani; S. Antonaroli; M. Burattini; P. Paoli; P. Rossi. - In: DALTON TRANSACTIONS. - ISSN 1477-9226. - STAMPA. - 39:(2010), pp. 3665-3672. [10.1039/b913130b]

Palladium complexes with a tridentate PNO ligand. Synthesis of eta 1-allyl complexes and cross-coupling reactions promoted by boron compounds

PAOLI, PAOLA;ROSSI, PATRIZIA
2010

Abstract

The iminophosphine 2-(2-Ph2P)C6H4N=CHC6H4OH (P-N-OH) reacts with [Pd(m-Cl)(h3-C3H5)]2 yielding [PdCl(P-N-O)] and propene. In the presence of NEt3, the reaction of P-N-OH with [Pd(m-Cl)(h3-1-R1,3-R2C3H3)]2 (R1 = R2 = H, Ph; R1 = H, R2 = Ph) affords the h1-allyl derivatives [Pd(h1-1-R1,3-R2C3H3)](P-N-O)] (R1 = R2 = H: 1; R1 = H, R2 = Ph: 2; R1 = R2 = Ph: 3). In solution, the complexes 1 and 3 undergo a slow dynamic process which interconverts the bonding site of the allyl ligand. The X-ray structural analysis of 1 indicates a square-planar coordination geometry around the palladium centre with a P,N,O,-tridentate ligand and a s bonded allyl group. The complexes [PdR(P-N-O)] (R = C6H4Me-4, C≡CPh) react slowly with p-bromoanisole in the presence of p-tolylboronic acid to give [PdBr(P-N-O)] and the coupling product RC6H4OMe-4. The latter reactions also proceed at a low rate under catalytic conditions. The coupling of allyl bromide with p-tolylboronic acid is catalyzed by [PdCl(P-N-O)]/K2CO3 to give 4-allyltoluene.
2010
39
3665
3672
B. Crociani; S. Antonaroli; M. Burattini; P. Paoli; P. Rossi
File in questo prodotto:
File Dimensione Formato  
65.pdf

Accesso chiuso

Tipologia: Versione finale referata (Postprint, Accepted manuscript)
Licenza: Tutti i diritti riservati
Dimensione 352.81 kB
Formato Adobe PDF
352.81 kB Adobe PDF   Richiedi una copia

I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/385762
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 20
  • ???jsp.display-item.citation.isi??? 20
social impact