Sterically hindered selenoether ligands: Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling

Umesh Kumar; Pooja Dubey; Ved Vati Singh; Om Prakash; Ajai K. Singh

doi:10.1039/c4ra06313a

Sterically hindered selenoether ligands: Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling

Umesh Kumar, Pooja Dubey, Ved Vati Singh, Om Prakash, Ajai K. Singh

Research output: Contribution to journal › Article › peer-review

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Abstract

2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH₂CH₂NH₂resulting in a sterically hindered selenoether ligand (Schiff base) [2-HO-3,5-(C(CH₃)₃)₂-C₆H₂-CN-(CH₂)₂SePh] (L1)/[2-PhCH₂O-3,5-(C(CH₃)₃)₂-C₆H₂-CH₂-NH-(CH₂)₂SePh] (L2). The reactions of L1 and L2 with Na₂PdCl₄in methanol and acetone-water mixture at room temperature have resulted in complexes [PdCl (L1-H)] (1) and [PdCl₂(L2)] (2)], respectively. Both the complexes and their ligands have been characterized with ¹H, ¹³C{¹H} and ⁷⁷Se{¹H} NMR spectroscopy. The molecular structures of complexes 1 and 2 have been determined with single crystal X-ray diffraction. The Pd-Se bond lengths in 1 and 2 are 2.370(1) and 2.366(1) Å, respectively. The geometry around palladium in both the complexes is nearly square planar. Complexes 1 and 2 (0.1 mol% Pd) have been found efficient as catalysts for Suzuki-Miyaura C-C coupling reactions in the presence of K₂CO₃in ethanol. The catalysis in water with complex 1 in the presence of K₂CO₃was found feasible but with low conversion (up to 40%). The efficiency of 1 in carrying out the coupling is marginally better than that of 2.

Original language	English
Pages (from-to)	41659-41665
Number of pages	7
Journal	RSC Advances
Volume	40
Issue number	78
DOIs	https://doi.org/10.1039/c4ra06313a
State	Published - 1 Jan 2014
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/c4ra06313a

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title = "Sterically hindered selenoether ligands: Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling",

abstract = "2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH2CH2NH2resulting in a sterically hindered selenoether ligand (Schiff base) [2-HO-3,5-(C(CH3)3)2-C6H2-CN-(CH2)2SePh] (L1)/[2-PhCH2O-3,5-(C(CH3)3)2-C6H2-CH2-NH-(CH2)2SePh] (L2). The reactions of L1 and L2 with Na2PdCl4in methanol and acetone-water mixture at room temperature have resulted in complexes [PdCl (L1-H)] (1) and [PdCl2(L2)] (2)], respectively. Both the complexes and their ligands have been characterized with 1H, 13C{1H} and 77Se{1H} NMR spectroscopy. The molecular structures of complexes 1 and 2 have been determined with single crystal X-ray diffraction. The Pd-Se bond lengths in 1 and 2 are 2.370(1) and 2.366(1) {\AA}, respectively. The geometry around palladium in both the complexes is nearly square planar. Complexes 1 and 2 (0.1 mol% Pd) have been found efficient as catalysts for Suzuki-Miyaura C-C coupling reactions in the presence of K2CO3in ethanol. The catalysis in water with complex 1 in the presence of K2CO3was found feasible but with low conversion (up to 40%). The efficiency of 1 in carrying out the coupling is marginally better than that of 2.",

author = "Umesh Kumar and Pooja Dubey and Singh, {Ved Vati} and Om Prakash and Singh, {Ajai K.}",

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T2 - Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling

AU - Kumar, Umesh

AU - Dubey, Pooja

AU - Singh, Ved Vati

AU - Prakash, Om

AU - Singh, Ajai K.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - 2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH2CH2NH2resulting in a sterically hindered selenoether ligand (Schiff base) [2-HO-3,5-(C(CH3)3)2-C6H2-CN-(CH2)2SePh] (L1)/[2-PhCH2O-3,5-(C(CH3)3)2-C6H2-CH2-NH-(CH2)2SePh] (L2). The reactions of L1 and L2 with Na2PdCl4in methanol and acetone-water mixture at room temperature have resulted in complexes [PdCl (L1-H)] (1) and [PdCl2(L2)] (2)], respectively. Both the complexes and their ligands have been characterized with 1H, 13C{1H} and 77Se{1H} NMR spectroscopy. The molecular structures of complexes 1 and 2 have been determined with single crystal X-ray diffraction. The Pd-Se bond lengths in 1 and 2 are 2.370(1) and 2.366(1) Å, respectively. The geometry around palladium in both the complexes is nearly square planar. Complexes 1 and 2 (0.1 mol% Pd) have been found efficient as catalysts for Suzuki-Miyaura C-C coupling reactions in the presence of K2CO3in ethanol. The catalysis in water with complex 1 in the presence of K2CO3was found feasible but with low conversion (up to 40%). The efficiency of 1 in carrying out the coupling is marginally better than that of 2.

AB - 2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH2CH2NH2resulting in a sterically hindered selenoether ligand (Schiff base) [2-HO-3,5-(C(CH3)3)2-C6H2-CN-(CH2)2SePh] (L1)/[2-PhCH2O-3,5-(C(CH3)3)2-C6H2-CH2-NH-(CH2)2SePh] (L2). The reactions of L1 and L2 with Na2PdCl4in methanol and acetone-water mixture at room temperature have resulted in complexes [PdCl (L1-H)] (1) and [PdCl2(L2)] (2)], respectively. Both the complexes and their ligands have been characterized with 1H, 13C{1H} and 77Se{1H} NMR spectroscopy. The molecular structures of complexes 1 and 2 have been determined with single crystal X-ray diffraction. The Pd-Se bond lengths in 1 and 2 are 2.370(1) and 2.366(1) Å, respectively. The geometry around palladium in both the complexes is nearly square planar. Complexes 1 and 2 (0.1 mol% Pd) have been found efficient as catalysts for Suzuki-Miyaura C-C coupling reactions in the presence of K2CO3in ethanol. The catalysis in water with complex 1 in the presence of K2CO3was found feasible but with low conversion (up to 40%). The efficiency of 1 in carrying out the coupling is marginally better than that of 2.

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DO - 10.1039/c4ra06313a

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VL - 40

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JO - RSC Advances

JF - RSC Advances

IS - 78

ER -

Sterically hindered selenoether ligands: Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling

Abstract

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