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Reactivity of 6-(2-tolyl)- and 6-(2,6-xylyl)-2,2′-bipyridines with palladium(II) derivatives: selective C(sp3)---H vs. C(sp2)---H activation

Stoccoro, Sergio and Soro, Barbara and Minghetti, Giovanni and Zucca, Antonio and Cinellu, Maria Agostina (2003) Reactivity of 6-(2-tolyl)- and 6-(2,6-xylyl)-2,2′-bipyridines with palladium(II) derivatives: selective C(sp3)---H vs. C(sp2)---H activation. Journal of Organometallic Chemistry, Vol. 679 (1), p. 1-9. ISSN 0022-328X. Article.

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DOI: 10.1016/S0022-328X(03)00457-1

Abstract

Two new 6-substituted 2,2′-bipyridines, L, 6-(2-tolyl)bipy, L1, and 6-(2,6-xylyl)bipy, L2, have been synthesized. Their reactions with Na2[PdCl4] or {Pd(OAc)2} afford either 1:1 adducts [Pd(L)X2] (X=Cl, OAc) or five-membered cyclometallated derivatives [Pd(L1-H)X] arising from C(sp2)---H activation. From the chloro-alkyl intermediates [Pd(L)(Me)Cl], in the presence of Na[BAr′4] (Ar′=3,5-(CF3)2C6H3), cationic species [Pd(L)(Me)(S)]+ (L=L1, L2; S=CH3CN) can be obtained. At variance, in less coordinating solvents, e.g. dichloromethane, unexpected activation of a C(sp3)---H bond occurs with loss of methane, to afford 6-membered cyclometallated derivatives. The latter species were isolated as [Pd(L-H)(PPh3)][BAr′4].

Item Type:Article
ID Code:4919
Status:Published
Refereed:Yes
Uncontrolled Keywords:Cyclometallation, 2,2′-bipyridine, palladium
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Elsevier Science
ISSN:0022-328X
Deposited On:22 Nov 2010 16:35

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