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C-H activation at the 3-position of pentane chains to form [N-C(sp3)-N]- complexes incorporating six-membered pallada(II)cyclic rings and pyridine, pyrazole and N-methylimidazole donor groups. Structural studies and comparison with [N-C(sp2)-N]- complexes

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Canty, AJ, Patel, J, Skelton, BW and White, AH 2000 , 'C-H activation at the 3-position of pentane chains to form [N-C(sp3)-N]- complexes incorporating six-membered pallada(II)cyclic rings and pyridine, pyrazole and N-methylimidazole donor groups. Structural studies and comparison with [N-C(sp2)-N]- complexes' , Journal of Organometallic Chemistry, vol. 607, No. 1 - 2 , pp. 194-202 , doi: 10.1016/S0022-328X(00)00338-7.

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Abstract

Alkylpalladium complexes bearing the [N-C(sp3)-N]- donor motif and two six-membered palladacycles are generated on
activation of C(sp3)-H bonds by palladium(II) acetate. Cyclopalladation of the new reagents 1,5-bis(pyridin-2-yl)pentane [CH2(CH2CH2py)2] (1), 1,5-bis(pyrazol-1-yl)pentane [CH2(CH2CH2pz)2] (2) and 1,5-bis(N-methylimidazol-2-yl)pentane [CH2(CH2CH2mim)2] (3), followed by reaction with lithium chloride afford the palladium(II) complexes Pd{CH(CH2CH2py)2- N,C,N'}Cl (5), Pd{CH(CH2CH2pz)2-N,C,N'}Cl (6) and Pd{CH(CH2CH2mim)2-N,C,N'}Cl (7), respectively. Abstraction of chloride from 6 with AgBF4 in acetone generates the cationic acetone complex [Pd{CH(CH2CH2pz)2-N,C,N'}(OCMe2)][BF4] (8). X-ray crystal structures of 5, 6 and 8 reveal tridentate [N-C(sp3)-N']- intramolecular coordination of the ligands. These structures
are compared with that of a closely related [N-C(sp2)-N]- system in [Pd{2,6-(pzCH2)2C6H3-N,C,N'}(OH2)][BF4] (10), obtained on cyclopalladation of 1,3-bis(pyrazol-1-ylmethyl)benzene followed by derivatisation to form the aqua complex.

Item Type: Article
Authors/Creators:Canty, AJ and Patel, J and Skelton, BW and White, AH
Journal or Publication Title: Journal of Organometallic Chemistry
ISSN: 0022-328X
DOI / ID Number: 10.1016/S0022-328X(00)00338-7
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The original publication is available at www.springerlink.com

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