Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation

Nawaz, Zahid; Gürbüz, Nevin; Naveed, Muhammad; Özdemir, Namık; Cetinkaya, Bekir; Özdemir, İsmail

doi:10.55730/1300-0527.3606

Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation

Zahid NAWAZ, (Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan)

Nevin GÜRBÜZ, (İnönü Üniversitesi, Kataliz Araştırma ve Uygulama Merkezi, Malatya, Türkiye)

Muhammad Naveed ZAFAR, (Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan)

Namık ÖZDEMİR, (Ondokuz Mayıs Üniversitesi, Eğitim Fakültesi, Matematik ve Fen Bilimleri Eğitimi Bölümü, Samsun, Türkiye)

Bekir ÇETİNKAYA, (Ege Üniversitesi, Fen Fakültesi, Kimya Bölümü, İzmir, Türkiye)

İsmail ÖZDEMİR (İnönü Üniversitesi, Kataliz Araştırma ve Uygulama Merkezi, Malatya, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2023 Cilt: 47 Sayı: 5 Sayfa Aralığı: 1209 - 1223 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3606 İndeks Tarihi: 21-11-2023

Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation

Öz:

A low temperature hydrogen borrowing approach to generate secondary amines using benzimidazole-based N-heterocyclic carbene (BNHC) ruthenium complexes is reported. A series of the piano-stool complexes of the type $[(η^6-p-cymene)(BNHC)RuCl_2]$ (1a–g) were synthesized via one-pot reaction of the NHC salt precursor, $$Ag_2O, and [RuCl_2(p-cymene)]_2$ and characterized using con- ventional spectroscopic techniques. The geometry of two precursors, $[( η^6-p-cymene)(^{Me4Bn}Me2BNHC^{CH2OxMe})RuCl2]$ ( 1f) and $[( η^6-p- cymene)(^{Me5Bn}Me_2BNHC^{CH2OxMe})RuCl_2]$ (1g), was studied by single crystal X-ray diffraction. These catalysts were found to dehydrogenate alcohols efficiently at temperatures as low as 50 °C to allow Schiff-base condensation and subsequent imine hydrogenation to afford secondary amines. Notably, this ruthenium-based procedure enables the N-alkylation of aromatic and heteroaromatic primary amines with a wide range of primary alcohols in excellent yields of up to 98%. The present methodology is green and water is liberated as the sole byproduct.

Anahtar Kelime: Benzimidazol-2-ylidenes ruthenium complexes amine alkylation C–N bond formation mild conditions

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	Nawaz Z, Gürbüz N, Naveed M, Özdemir N, Cetinkaya B, Özdemir İ (2023). Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. , 1209 - 1223. 10.55730/1300-0527.3606
Chicago	Nawaz Zahid,Gürbüz Nevin,Naveed Muhammad,Özdemir Namık,Cetinkaya Bekir,Özdemir İsmail Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. (2023): 1209 - 1223. 10.55730/1300-0527.3606
MLA	Nawaz Zahid,Gürbüz Nevin,Naveed Muhammad,Özdemir Namık,Cetinkaya Bekir,Özdemir İsmail Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. , 2023, ss.1209 - 1223. 10.55730/1300-0527.3606
AMA	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. . 2023; 1209 - 1223. 10.55730/1300-0527.3606
Vancouver	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. . 2023; 1209 - 1223. 10.55730/1300-0527.3606
IEEE	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ "Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation." , ss.1209 - 1223, 2023. 10.55730/1300-0527.3606
ISNAD	Nawaz, Zahid vd. "Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation". (2023), 1209-1223. https://doi.org/10.55730/1300-0527.3606

APA	Nawaz Z, Gürbüz N, Naveed M, Özdemir N, Cetinkaya B, Özdemir İ (2023). Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. Turkish Journal of Chemistry, 47(5), 1209 - 1223. 10.55730/1300-0527.3606
Chicago	Nawaz Zahid,Gürbüz Nevin,Naveed Muhammad,Özdemir Namık,Cetinkaya Bekir,Özdemir İsmail Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. Turkish Journal of Chemistry 47, no.5 (2023): 1209 - 1223. 10.55730/1300-0527.3606
MLA	Nawaz Zahid,Gürbüz Nevin,Naveed Muhammad,Özdemir Namık,Cetinkaya Bekir,Özdemir İsmail Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. Turkish Journal of Chemistry, vol.47, no.5, 2023, ss.1209 - 1223. 10.55730/1300-0527.3606
AMA	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. Turkish Journal of Chemistry. 2023; 47(5): 1209 - 1223. 10.55730/1300-0527.3606
Vancouver	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation. Turkish Journal of Chemistry. 2023; 47(5): 1209 - 1223. 10.55730/1300-0527.3606
IEEE	Nawaz Z,Gürbüz N,Naveed M,Özdemir N,Cetinkaya B,Özdemir İ "Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation." Turkish Journal of Chemistry, 47, ss.1209 - 1223, 2023. 10.55730/1300-0527.3606
ISNAD	Nawaz, Zahid vd. "Benzimidazol-2-ylidene ruthenium complexes for C–N bond formation through alcohol dehydrogenation". Turkish Journal of Chemistry 47/5 (2023), 1209-1223. https://doi.org/10.55730/1300-0527.3606