Organo-palladium(II) complexes bearing unsymmetrical N,N,N-pincer ligands: synthesis, structures and oxidatively induced coupling reactions

Wright, L.A., Hope, E.G., Solan, G.A., Cross, W.B. ORCID: 0000-0001-6277-400X and Singh, K., 2015. Organo-palladium(II) complexes bearing unsymmetrical N,N,N-pincer ligands: synthesis, structures and oxidatively induced coupling reactions. Dalton Transcations, 44 (16), pp. 7230-7241. ISSN 1477-9226

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Abstract

The 2-(2'-aniline)-6-imine-pyridines, 2-(C6H4--2'-NH2)-6-(CMe=NAr)C5H3 N (Ar = 4-i-PrC6H4 (HL1a), 2,6-i-Pr2C6H3 (HL1b)), have been synthesised via sequential Stille cross-coupling, deprotection and condensation steps from 6-tributylstannyl-2-(2-methyl-1,3-dioxolan-2-yl)pyridine and 2-bromonitrobenzene. The palladium(II) acetate N,N,N-pincer complexes, [{2-(C6H4-2'-NH)-6-(CMe=NAr)C5H3N}Pd(OAc)] (Ar = 4-i-PrC6H4 (1a), 2,6-i-Pr2C6H3 (1b)), can be prepared by reacting HL1 with Pd(OAc) 2 or, in the case of 1a , more conveniently by the template reaction of ketone 2-(C6H4-2'-NH2)-6-(CMe=O)C5H3N, Pd(OAc)2 and 4-isopropylaniline; ready conversion of 1 to their chloride analogues, [{2-(C6H4-2'-NH)-6-(CMe=NAr)C5H3N}PdCl] (Ar = 4-i-PrC6H4 (2a), 2,6-i-Pr2C6H3 (2b)), has been demonstrated. The phenyl-containing complexes, [{2-(C6H4-2'-NH)-6-(CMe=NAr)C5H3N}PdPh] (Ar = 4-i-PrC6H4 (3a), 2,6-i-Pr2C6H3 (3b)), can be obtained by treating HL1 with (PPh3)2 PdPh(Br) in the presence of NaH or with regard to 3a, by the salt elimination reaction of 2a with phenyllithium.

Item Type: Journal article
Publication Title: Dalton Transcations
Creators: Wright, L.A., Hope, E.G., Solan, G.A., Cross, W.B. and Singh, K.
Publisher: Royal Society of Chemistry
Place of Publication: Cambridge
Date: 2015
Volume: 44
Number: 16
ISSN: 1477-9226
Identifiers:
NumberType
10.1039/c5dt00216hDOI
Divisions: Schools > School of Science and Technology
Depositing User: EPrints Services
Date Added: 09 Oct 2015 10:55
Last Modified: 09 Jun 2017 13:44
URI: http://irep.ntu.ac.uk/id/eprint/20197

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