Metal-free synthesis of methylene-bridged bis-1,3-dicarbonyl compounds via oxidative C–C bond cleavage of tertiary aliphatic amines

RSC Advances ◽  
2014 ◽  
Vol 4 (51) ◽  
pp. 26783-26786 ◽  
Author(s):  
Li-Juan Xing ◽  
Xi-Mei Wang ◽  
Hong-Ying Li ◽  
Wen Zhou ◽  
Ning Kang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Oxidative Reaction ◽  
Metal Free

A metal-free Bu4NI mediated oxidative reaction utilizing tertiary aliphatic amines and 1,3-dicarbonyl compounds for the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds has been developed. This reaction involved an unexpected C–C bond cleavage of tertiary aliphatic amines.

ChemInform Abstract: Metal-Free Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds via Oxidative C-C Bond Cleavage of Tertiary Aliphatic Amines.

ChemInform ◽  
2015 ◽  
Vol 46 (5) ◽  
pp. no-no
Author(s):  
Li-Juan Xing ◽  
Xi-Mei Wang ◽  
Hong-Ying Li ◽  
Wen Zhou ◽  
Ning Kang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Aliphatic Amines ◽  
Dicarbonyl Compounds ◽  
Metal Free

scholarly journals Stereoselective Tandem Iridium-Catalyzed Alkene Isomerization-Cope Rearrangement of ω-diene Epoxides: Efficient Access to Acyclic 1,6-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Rahul Suresh ◽  
Itai Massad ◽  
Ilan Marek
Keyword(s):  
Bond Cleavage ◽  
Cope Rearrangement ◽  
Dicarbonyl Compounds ◽  
Alkene Isomerization ◽  
Efficient Access

The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4- positions. We employ...

Bifunctional metal-free photo-organocatalysts for enantioselective aerobic oxidation of β-dicarbonyl compounds

Tetrahedron ◽  
2018 ◽  
Vol 74 (27) ◽  
pp. 3624-3633 ◽  
Author(s):  
Xiao-fei Tang ◽  
Shi-hao Feng ◽  
Ya-kun Wang ◽  
Fan Yang ◽  
Ze-hao Zheng ◽  
...  
Keyword(s):  
Aerobic Oxidation ◽  
Dicarbonyl Compounds ◽  
Metal Free

Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Synthesis ◽  
2021 ◽  
Author(s):  
Wey-Chyng Jeng ◽  
Po-Chung Chien ◽  
Sandip Sambhaji Vagh ◽  
Athukuri Edukondalu ◽  
Wenwei Lin
Keyword(s):  
Intramolecular Cyclization ◽  
Efficient Method ◽  
Bond Cleavage ◽  
Scale Up ◽  
Acyl Chlorides ◽  
Metal Free ◽  
Mild Conditions ◽  
Synthetic Utility ◽  
Mechanistic Investigations ◽  
Synthetic Transformations

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides in the presence of base-catalyzed by organophosphanes. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under metal-free and mild conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/ rearrangement sequence. The mechanistic investigations revealed that the C-O bond cleavage on possible betaine intermediate is the key step for the installation of keto-functionality at β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by scale-up reactions and synthetic transformations of the products.

A Formal Metal-Free γ-Arylation of 1,3-Dicarbonyl Compounds via a Sequence of Isomerization/1,4-Addition/[3,3]-Sigmatropic Rearrangement

2021 ◽  
Author(s):  
Shi-Chao Lu ◽  
Fuqiang Wen ◽  
Xidong Guan
Keyword(s):  
Sigmatropic Rearrangement ◽  
Mechanistic Studies ◽  
Dicarbonyl Compounds ◽  
Metal Free

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide an unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a...

Dinuclear cobalt complexes supported by biphenol and binaphthol-derived bis(salicylaldimine) ligands: synthesis, characterization and catalytic application in β-enaminone synthesis from 1,3-dicarbonyl compounds and aliphatic amines

2020 ◽  
Vol 44 (35) ◽  
pp. 15109-15121
Author(s):  
Adelew Estifanos Filkale ◽  
Chandni Pathak
Keyword(s):  
Cobalt Complexes ◽  
Aliphatic Amines ◽  
Ambient Conditions ◽  
Dicarbonyl Compounds ◽  
Catalytic Application ◽  
Scaffolding Ligands

Biaryl scaffolding ligands form dicobalt clusters, which serve as efficient catalysts in enaminone synthesis under ambient conditions.

Diiodine-Mediated Oxidative Reaction for the Construction of Imidazo[1,5-a]pyridines under Metal-Free Conditions

Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 695-698 ◽  
Author(s):  
Kexin Su ◽  
Mingda Qin ◽  
Yongxin Chen ◽  
Yafeng Liu ◽  
Yuan Tian ◽  
...  
Keyword(s):  
Oxidative Dehydrogenation ◽  
Oxidative Reaction ◽  
Metal Free

An efficient and general protocol has been developed for preparing imidazo[1,5-a]pyridines in moderate to excellent yields by an I2-mediated sequential dual oxidative C(sp3)–H amination of ethyl pyridin-2-ylacetates with benzylamines. The metal- and peroxide-free reaction involves oxidative dehydrogenation and two C–N couplings.

I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2018-2023 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Tongle Shao ◽  
Jun Zhou ◽  
Chen Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Oxidation Pathway ◽  
Keto Esters ◽  
Oxidative Coupling Reaction

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

scholarly journals Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transfer Reaction ◽  
Bond Cleavage ◽  
Electron Transfer Reaction ◽  
Amide Bond ◽  
Single Electron Transfer ◽  
Reaction Conditions ◽  
Metal Free ◽  
Single Electron Transfer Reaction

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

Sign in / Sign up

Export Citation Format

Share Document