Substituted (pyridinyl)benzoazole palladium complexes: Synthesis and application as Heck coupling catalysts

Stephen O. Ojwach; Gunnar Westman; James Darkwa

doi:10.1016/j.poly.2007.08.033

Substituted (pyridinyl)benzoazole palladium complexes: Synthesis and application as Heck coupling catalysts

Stephen O. Ojwach, Gunnar Westman, James Darkwa

Chemical Sciences

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

9 Citations (Scopus)

Abstract

The synthesis of 2-(4-tert-butylpyridin-2-yl)-benzooxazole (L3), 2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L4) and 6-tert-Butyl-2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L5) by intramolecular cyclization under basic conditions is described. Reactions of 2-pyridin-2-yl-1H-benzoimidazole (L1), 2-pyridin-2-yl-benzothiazole (L2) and L3-L5 with either [Pd(NCMe)₂Cl₂] or [Pd(COD)MeCl] afforded the corresponding mononuclear palladium complexes [Pd(L1)MeCl] (1), [Pd(L2)MeCl] (2), [Pd(L3)Cl₂] (3), [Pd(L3)MeCl] (4), [Pd(L4)Cl₂] (5), [Pd(L4)MeCl] (6) and [Pd(L4)MeCl] (7) as confirmed by mass spectrometry and elemental analyses. The palladium complexes are efficient Heck coupling catalysts for the reaction of iodobenzene with butylacrylate under mild conditions. Benzothiazole and benzooxazole containing complexes show faster induction periods compared to the benzoimidazole analogues.

Original language	English
Pages (from-to)	5544-5552
Number of pages	9
Journal	Polyhedron
Volume	26
Issue number	18
DOIs	https://doi.org/10.1016/j.poly.2007.08.033
Publication status	Published - 20 Nov 2007

Keywords

Benzoazoles ligands
Catalysts
Heck coupling reactions
Palladium complexes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.poly.2007.08.033

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@article{b403ec34062441fd910f25d09099724e,

title = "Substituted (pyridinyl)benzoazole palladium complexes: Synthesis and application as Heck coupling catalysts",

abstract = "The synthesis of 2-(4-tert-butylpyridin-2-yl)-benzooxazole (L3), 2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L4) and 6-tert-Butyl-2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L5) by intramolecular cyclization under basic conditions is described. Reactions of 2-pyridin-2-yl-1H-benzoimidazole (L1), 2-pyridin-2-yl-benzothiazole (L2) and L3-L5 with either [Pd(NCMe)2Cl2] or [Pd(COD)MeCl] afforded the corresponding mononuclear palladium complexes [Pd(L1)MeCl] (1), [Pd(L2)MeCl] (2), [Pd(L3)Cl2] (3), [Pd(L3)MeCl] (4), [Pd(L4)Cl2] (5), [Pd(L4)MeCl] (6) and [Pd(L4)MeCl] (7) as confirmed by mass spectrometry and elemental analyses. The palladium complexes are efficient Heck coupling catalysts for the reaction of iodobenzene with butylacrylate under mild conditions. Benzothiazole and benzooxazole containing complexes show faster induction periods compared to the benzoimidazole analogues.",

keywords = "Benzoazoles ligands, Catalysts, Heck coupling reactions, Palladium complexes",

author = "Ojwach, {Stephen O.} and Gunnar Westman and James Darkwa",

year = "2007",

month = nov,

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doi = "10.1016/j.poly.2007.08.033",

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journal = "Polyhedron",

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T1 - Substituted (pyridinyl)benzoazole palladium complexes

T2 - Synthesis and application as Heck coupling catalysts

AU - Ojwach, Stephen O.

AU - Westman, Gunnar

AU - Darkwa, James

PY - 2007/11/20

Y1 - 2007/11/20

N2 - The synthesis of 2-(4-tert-butylpyridin-2-yl)-benzooxazole (L3), 2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L4) and 6-tert-Butyl-2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L5) by intramolecular cyclization under basic conditions is described. Reactions of 2-pyridin-2-yl-1H-benzoimidazole (L1), 2-pyridin-2-yl-benzothiazole (L2) and L3-L5 with either [Pd(NCMe)2Cl2] or [Pd(COD)MeCl] afforded the corresponding mononuclear palladium complexes [Pd(L1)MeCl] (1), [Pd(L2)MeCl] (2), [Pd(L3)Cl2] (3), [Pd(L3)MeCl] (4), [Pd(L4)Cl2] (5), [Pd(L4)MeCl] (6) and [Pd(L4)MeCl] (7) as confirmed by mass spectrometry and elemental analyses. The palladium complexes are efficient Heck coupling catalysts for the reaction of iodobenzene with butylacrylate under mild conditions. Benzothiazole and benzooxazole containing complexes show faster induction periods compared to the benzoimidazole analogues.

AB - The synthesis of 2-(4-tert-butylpyridin-2-yl)-benzooxazole (L3), 2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L4) and 6-tert-Butyl-2-(4-tert-butyl-pyridin-2-yl)-benzothiazole (L5) by intramolecular cyclization under basic conditions is described. Reactions of 2-pyridin-2-yl-1H-benzoimidazole (L1), 2-pyridin-2-yl-benzothiazole (L2) and L3-L5 with either [Pd(NCMe)2Cl2] or [Pd(COD)MeCl] afforded the corresponding mononuclear palladium complexes [Pd(L1)MeCl] (1), [Pd(L2)MeCl] (2), [Pd(L3)Cl2] (3), [Pd(L3)MeCl] (4), [Pd(L4)Cl2] (5), [Pd(L4)MeCl] (6) and [Pd(L4)MeCl] (7) as confirmed by mass spectrometry and elemental analyses. The palladium complexes are efficient Heck coupling catalysts for the reaction of iodobenzene with butylacrylate under mild conditions. Benzothiazole and benzooxazole containing complexes show faster induction periods compared to the benzoimidazole analogues.

KW - Benzoazoles ligands

KW - Catalysts

KW - Heck coupling reactions

KW - Palladium complexes

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U2 - 10.1016/j.poly.2007.08.033

DO - 10.1016/j.poly.2007.08.033

M3 - Article

AN - SCOPUS:35549009433

SN - 0277-5387

VL - 26

SP - 5544

EP - 5552

JO - Polyhedron

JF - Polyhedron

IS - 18

ER -

Substituted (pyridinyl)benzoazole palladium complexes: Synthesis and application as Heck coupling catalysts

Abstract

Keywords

ASJC Scopus subject areas

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