TY - JOUR
T1 - Reactivity of 2-(2-hydroxyphenyl)benzoxazole and 2-(2-hydroxyphenyl)benzothiazole towards group 10 transition metals. Evaluation in palladium catalyzed Suzuki-Miyaura C-C couplings
AU - Valdés, Hugo
AU - Reyes-Martínez, Reyna
AU - Pioquinto-Mendoza, J. Roberto
AU - Avila-Sorrosa, Alcives
AU - Toscano, Rubén A.
AU - Hernández-Ortega, Simón
AU - Morales-Morales, David
N1 - Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.
PY - 2015/5/26
Y1 - 2015/5/26
N2 - A series of group 10 transition metal complexes based on 2-(2-hydroxyphenyl)benzoxazole (HPBO) and 2-(2-hydroxyphenyl)benzothiazole (HPBT) have been prepared. Reactions of nickel or palladium acetates with HPBT and HPBO produce chelate N-O coordinated compounds respectively. Whilst reaction of [K2PtCl4] with HPBT affords organometallic species product of a C-H bond activation of the phenolic moiety at room temperature. The molecular structures of the three complexes were unambiguously determined by means of single crystal X-ray diffraction analyses. The nickel compound [{Ni(κ2-N,O-HPBT)}2(μ2-O-HPBT)2(μ2-OOCCH3)] (1) showing to be binuclear with the nickel ions found in six-coordinated distorted octahedral environments. Conversely, compound [Pd(κ2-N,O-HPBO)2] (2) is a tetracoordinated monomer with the Pd center having a slightly distorted square planar geometry. Similarly, platinacycle [Pt(κ1-N-HPBT)(κ2-N,C-HPBT)Cl] (3) shows the Pt center into a slightly distorted square planar geometry, exhibiting ligand HPBT in two different coordination modes, as single κ1-N coordinated and as κ2-N-C metalated chelate bidentate ligand, completing the coordination sphere with a chloride ligand. The catalytic activity of the palladium complex (2) was evaluated in Suzuki-Miyaura cross couplings, showing good activity.
AB - A series of group 10 transition metal complexes based on 2-(2-hydroxyphenyl)benzoxazole (HPBO) and 2-(2-hydroxyphenyl)benzothiazole (HPBT) have been prepared. Reactions of nickel or palladium acetates with HPBT and HPBO produce chelate N-O coordinated compounds respectively. Whilst reaction of [K2PtCl4] with HPBT affords organometallic species product of a C-H bond activation of the phenolic moiety at room temperature. The molecular structures of the three complexes were unambiguously determined by means of single crystal X-ray diffraction analyses. The nickel compound [{Ni(κ2-N,O-HPBT)}2(μ2-O-HPBT)2(μ2-OOCCH3)] (1) showing to be binuclear with the nickel ions found in six-coordinated distorted octahedral environments. Conversely, compound [Pd(κ2-N,O-HPBO)2] (2) is a tetracoordinated monomer with the Pd center having a slightly distorted square planar geometry. Similarly, platinacycle [Pt(κ1-N-HPBT)(κ2-N,C-HPBT)Cl] (3) shows the Pt center into a slightly distorted square planar geometry, exhibiting ligand HPBT in two different coordination modes, as single κ1-N coordinated and as κ2-N-C metalated chelate bidentate ligand, completing the coordination sphere with a chloride ligand. The catalytic activity of the palladium complex (2) was evaluated in Suzuki-Miyaura cross couplings, showing good activity.
KW - 2-(2-Hydroxyphenyl)benzothiazole
KW - 2-(2-Hydroxyphenyl)benzoxazole
KW - C-H activation
KW - Catalysis
KW - Crystal structures
KW - Suzuki-Miyaura couplings
UR - http://www.scopus.com/inward/record.url?scp=84929701910&partnerID=8YFLogxK
U2 - 10.1016/j.ica.2015.03.012
DO - 10.1016/j.ica.2015.03.012
M3 - Artículo
AN - SCOPUS:84929701910
SN - 0020-1693
VL - 431
SP - 222
EP - 229
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
ER -