Scandium Triflate Catalyzed Tandem Transfer Hydrogenation and Cyclization Reaction of o-Aminobenzaldehydes and o-Aminoacetophenone with Alcohols

Synthesis of Novel Bis-pyrazoles via Electrophilic Cyclization

Letters in Organic Chemistry ◽

10.2174/1570178615666181106155555 ◽

2019 ◽

Vol 16 (6) ◽

pp. 511-516

Author(s):

Adnan Cetin

Keyword(s):

13C Nmr ◽

Cyclization Reaction ◽

Electrophilic Cyclization ◽

Pyrazole Derivatives ◽

Spectral Analyses ◽

Mass Spectral ◽

Palladium Catalyzed ◽

Ft Ir ◽

Reaction Compound

Efficient steps towards the synthesis of novel (phenyl)(1'-aryl-1,5,5'-triphenyl[3,3'-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of α,β-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.

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Quaternary Carbon Center Forming [3 + 2] Cyclization Reaction by Adjusting the Substituents of Substrates

The Journal of Organic Chemistry ◽

10.1021/acs.joc.9b02041 ◽

2019 ◽

Vol 84 (21) ◽

pp. 13871-13880 ◽

Cited By ~ 3

Author(s):

Xie-Chao Yang ◽

Jin-Yu Liu ◽

Zhen Liu ◽

Xiu-Qin Hu ◽

Peng-Fei Xu

Keyword(s):

Cyclization Reaction ◽

Quaternary Carbon

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The unique substitution-cyclization reaction cascade inspired highly selective H2Sn probe development

Sensors and Actuators B Chemical ◽

10.1016/j.snb.2019.127382 ◽

2020 ◽

Vol 304 ◽

pp. 127382 ◽

Cited By ~ 1

Author(s):

Li Fu ◽

Chunfei Chen ◽

Wenqiang Chen ◽

Jun Huang ◽

Junan Xiao ◽

...

Keyword(s):

Cyclization Reaction

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New Stereoselective Entry to Azaspirocyclic Nucleus of Halichlorine and Pinnaic Acids by Radical Translocation/Cyclization Reaction

Organic Letters ◽

10.1021/ol034942v ◽

2003 ◽

Vol 5 (17) ◽

pp. 3017-3020 ◽

Cited By ~ 29

Author(s):

Kiyosei Takasu ◽

Hiroshi Ohsato ◽

Masataka Ihara

Keyword(s):

Cyclization Reaction

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Arene‐Immobilized Ru(II)/TsDPEN Complexes: Synthesis and Applications to the Asymmetric Transfer Hydrogenation of Ketones

European Journal of Inorganic Chemistry ◽

10.1002/ejic.202000948 ◽

2020 ◽

Author(s):

Simon Doherty ◽

Julian G. Knight ◽

Hind Alshaikh ◽

James Wilson ◽

Paul G. Waddell ◽

...

Keyword(s):

Transfer Hydrogenation ◽

Asymmetric Transfer Hydrogenation

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Mild and Selective Rhodium-Catalyzed Transfer Hydrogenation of Functionalized Arenes

Organic Letters ◽

10.1021/acs.orglett.1c00341 ◽

2021 ◽

Vol 23 (5) ◽

pp. 1910-1914

Author(s):

Yuhan Wang ◽

Zhiqian Chang ◽

Yan Hu ◽

Xiao Lin ◽

Xiaowei Dou

Keyword(s):

Transfer Hydrogenation

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Frontispiece: Escaping from Flatland: Stereoconvergent Synthesis of Three‐Dimensional Scaffolds via Ruthenium(II)‐Catalyzed Noyori–Ikariya Transfer Hydrogenation

Chemistry - A European Journal ◽

10.1002/chem.202180162 ◽

2021 ◽

Vol 27 (1) ◽

Author(s):

Andrej Emanuel Cotman

Keyword(s):

Three Dimensional ◽

Transfer Hydrogenation

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Highly dispersed CoNi alloy embedded in N‐doped graphitic carbon for the catalytic transfer hydrogenation of biomass‐derived furfural

Chemistry - An Asian Journal ◽

10.1002/asia.202100727 ◽

2021 ◽

Author(s):

Jun Wu ◽

Xinyue Yan ◽

Wenrui Wang ◽

Ming Jin ◽

Yuhang Xie ◽

...

Keyword(s):

Graphitic Carbon ◽

Transfer Hydrogenation ◽

Catalytic Transfer Hydrogenation ◽

Highly Dispersed ◽

Catalytic Transfer

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Recent developments on methanol as liquid organic hydrogen carrier in transfer hydrogenation reactions

Coordination Chemistry Reviews ◽

10.1016/j.ccr.2020.213728 ◽

2021 ◽

Vol 433 ◽

pp. 213728

Author(s):

Nidhi Garg ◽

Ankita Sarkar ◽

Basker Sundararaju

Keyword(s):

Transfer Hydrogenation ◽

Recent Developments ◽

Hydrogenation Reactions ◽

Hydrogen Carrier

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New Bifunctional Bis(azairidacycle) with Axial Chirality via Double Cyclometalation of 2,2′-Bis(aminomethyl)-1,1′-binaphthyl

Molecules ◽

10.3390/molecules26041165 ◽

2021 ◽

Vol 26 (4) ◽

pp. 1165

Author(s):

Yasuhiro Sato ◽

Yuichi Kawata ◽

Shungo Yasui ◽

Yoshihito Kayaki ◽

Takao Ikariya

Keyword(s):

Hydrogen Transfer ◽

Bond Cleavage ◽

Enantiomeric Excess ◽

Transfer Hydrogenation ◽

Catalyst Precursor ◽

Asymmetric Catalysts ◽

Axially Chiral ◽

Diastereomeric Mixture ◽

Raney Ni ◽

Half Sandwich

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C–N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5–C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 °C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C–H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.

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