Hydrosilylation Of (Hetero)aromatic Aldimines in the Presence of a Pd(I) Complex

Iovel, I.; Golomba, L.; Fleisher, M.; Popelis, J.; Grı̄nberga, Solveiga; Lukevics, É.

doi:10.1023/b:cohc.0000040765.61681.f0

Cited by 17 publications

(10 citation statements)

References 5 publications

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“…Imine compounds 5a , 5b , 5c were prepared according to literature [22]. o ‐Nitroaniline (2.486g, 18 mmol), benzaldehyde (1.592 g, 15 mmol), sulfuric acid (5 drops), and molecular sieves (15 g) were added to benzene (30 mL) in a 100‐mL round bottom flask.…”

Section: Methodsmentioning

confidence: 99%

“…The extract was then chromatographed on a silica gel column and eluted with hexane:EtOAc (85:15, 2% triethylamine) to give N ‐benzylidene‐2‐nitroaniline 5a (2.787g, 82%). The structure of N ‐benzylidene‐2‐nitroaniline 5a was determined by comparison of mp and 1 H NMR spectrum with those of literature [22]. Recrystallization from hexane gave yellow crystals, mp 70–71°C (ref.…”

Section: Methodsmentioning

confidence: 99%

“…Recrystallization from hexane gave yellow crystals, mp 70–71°C (ref. [22] mp 71–72°C); IR (KBr): 1594 cm −1 and 1334 cm −1 (NO 2 ); 1 H NMR (CDCl 3 ): δ 7.06 (d, J = 7.5 Hz, 1H, Ar‐H), 7.30 (dd, J = 7.5 Hz and 7.5 Hz, 1H, Ar‐H), 7.47–7.55 (m, 3H, 3 Ar‐H), 7.59 (dd, J = 7.5 Hz and 7.5 Hz, 1H, Ar‐H), 7.91 (d, J = 7.5 Hz, 2H, 2 Ar‐H), 7.96 (d, J = 7.5 Hz, 1H, Ar‐H), 8.41 (s, 1H, CHN); 13 C NMR (CDCl 3 ): δ 121.0 (d), 124.6 (d), 125.3 (d), 128.8 (d), 129.2 (d), 132.1 (d), 133.8 (d), 135.4 (s), 142.9 (s), 146.8 (s), 161.8 (d).…”

Section: Methodsmentioning

confidence: 99%

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Microwave‐assisted Cadogan reaction for the synthesis of 2‐aryl‐2H‐indazoles, 2‐aryl‐1H‐benzimidazoles, 2‐carbonylindoles, carbazole, and phenazine

Creencia

Kosaka

Muramatsu

et al. 2009

Journal of Heterocyclic Chem

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The Cadogan reaction, a widely accepted route for the synthesis of nitrogen containing heterocycles, is modified by using microwave radiation as the source of heat instead of the conventional heating by reflux in a nitrogen atmosphere for several hours. Appropriate starting materials were mixed with triethyl phosphite or triphenylphosphine and irradiated with microwaves for several minutes at a specific power to give the desired products. The indazoles were prepared by irradiating N‐(2‐nitrobenzylidene) anilines with triethyl phosphite at 200 W for 12–14 min to give 85–92% product yields. Irradiation of the mixture of N‐benzylidene‐2‐nitroanilines and triphenylphosphine at 200 W for 3–5 min yielded 93–96% of the benzimidazoles. The carbonylindoles were obtained in 61–68% yields by irradiating 2‐nitrochalcone or alkyl 2‐nitrocinnamates and triphenylphosphine with microwaves at 80–200 W for 8–11 min. The mixture of 2‐nitrobiphenyl and triphenylphosphine yielded 96% of carbazole when irradiated with microwaves at 200 W for 2 min while 75% of phenazine was obtained by irradiating the mixture of 2‐nitrodiphenylamine and triphenylphosphine with microwaves at 200 W for 3.5 min. These results show that microwave‐assisted Cadogan reactions gave better product yields at shorter reaction times. J. Heterocyclic Chem., (2009).

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Microwave‐assisted Cadogan reaction for the synthesis of 2‐aryl‐2H‐indazoles, 2‐aryl‐1H‐benzimidazoles, 2‐carbonylindoles, carbazole, and phenazine

Creencia

Kosaka

Muramatsu

et al. 2009

Journal of Heterocyclic Chem

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“…The hydrosilylation of aromatic nitro compounds has been less explored as compared to hydrosilylation of carbonyl derivatives . The hydrosilylation of nitro compounds have been studied using transition metal catalyst such as Pd, Pt, Rh, Sn, and Re catalysts …”

Section: Hydrosilylation Of Nitroarenesmentioning

confidence: 99%

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Shaikh¹

2019

ChemistrySelect

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Iron catalyzed organic synthesis has emerged as a sustainable chemistry due to the highly competitive cost, high natural abundance and ecologically acceptable properties of iron. Moreover, its extensive range of oxidation states i. e. -II to + VI provides numerous opportunities to perform multiple organic reactions. Recently iron catalysis has started competing the established precious metals. Among organic scaffolds, amines are important building blocks that are useful in the various fields starting from drugs, crop protection chemicals to dyes and pigments. Typically, hydrogenation or reduction of functional groups such as imines, amides, nitroarenes and nitriles results into amines. In this context, homogeneous iron catalyzed hydrosilylation is a highly promising alternative to traditional hydrogenation and other reduction reactions. This review is focused on the synthesis of amine and its derivatives via hydrosilylation of imines, amides, nitroarenes and nitriles using iron as a catalyst. Some of the reduction methods of these functional groups that may not follow the typical hydrosilylation pathway are also included in this review due to their strong relevance to the theme. The phenomenal progress in this focused area is summarized to witness this transformation towards sustainable development in the field of amine synthesis.

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“…The solid products were easily recrystallized from EtOH. In the case of oil products, EtOH was evaporated under reduced pressure to afford the essentially pure products (62,(81)(82)(83)(84)(85)(86)(87).…”

Section: Typical Procedures For the Synthesis Of Imine 5a-q Catalyzed mentioning

confidence: 99%

MCM-41 mesoporous silica: a highly efficient and recoverable catalyst for rapid synthesis of α-aminonitriles and imines

Eslami

Dekamin

Motlagh

et al. 2018

Green Chemistry Letters and Reviews

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In this work, pure MCM-41 mesoporous silica with active mesoporous sites has been successfully applied, as a highly efficient and recoverable catalyst, for the rapid and convenient synthesis of α-aminonitriles and imines. Various imines, as the intermediate of the Strecker reaction, were simply prepared from condensation of a wide range of aldehydes and amines in the presence of low loading of MCM-41 mesoporous silica under solvent-free conditions at room temperature in high to quantitative yields. Furthermore, the corresponding α-aminonitrile derivatives were prepared through the three-component Strecker reaction using trimethylsilylcyanide catalyzed by MCM-41 as a bifunctional heterogeneous mesoporous solid catalyst.

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Hydrosilylation Of (Hetero)aromatic Aldimines in the Presence of a Pd(I) Complex

Cited by 17 publications

References 5 publications

Microwave‐assisted Cadogan reaction for the synthesis of 2‐aryl‐2H‐indazoles, 2‐aryl‐1H‐benzimidazoles, 2‐carbonylindoles, carbazole, and phenazine

Microwave‐assisted Cadogan reaction for the synthesis of 2‐aryl‐2H‐indazoles, 2‐aryl‐1H‐benzimidazoles, 2‐carbonylindoles, carbazole, and phenazine

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

MCM-41 mesoporous silica: a highly efficient and recoverable catalyst for rapid synthesis of α-aminonitriles and imines

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