Rh(iii)-catalyzed redox-neutral annulation of azo and diazo compounds: one-step access to cinnolines

2016 ◽  
Vol 3 (1) ◽  
pp. 91-95 ◽  
Author(s):  
Peng Sun ◽  
Youzhi Wu ◽  
Yue Huang ◽  
Xiaoming Wu ◽  
Jinyi Xu ◽  
...  
Keyword(s):  
Bond Formation ◽  
Diazo Compounds ◽  
One Step

Cinnolines were synthesized in one step from azo and diazo compounds via a Rh(iii)-catalyzed redox-neutral C–H activation and C–N bond formation strategy.

scholarly journals Catalytic Three-component C–C Bond Forming Dearomatization of Bromoarenes with Malonates and Diazo Compounds

2020 ◽  
Author(s):  
Hiroki Kato ◽  
Itsuki Musha ◽  
Masaaki Komatsuda ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Present Method ◽  
Bond Formation ◽  
Diazo Compounds ◽  
Bond Forming ◽  
Rapid Access ◽  
Component C

A Pd-catalyzed dearomative three-component C–C bond formation of bromoarenes with diazo compounds and malonates was developed. Various bromoarenes ranging from benzenoids to azines and heteroles were transformed to the corresponding substituted alicyclic molecules. The key of this reaction is the generation of a benzyl-palladium intermediate, which reacts with malonates to form a Pd–<i>O</i>-enolate species. Strikingly, the present method enabled rapid access to multi-substituted alicycles through subsequent elaboration of dearomatized products.

One Step of Palladium Catalyzed Benzodioxane Ring C—O Bond Formation, Synthesis of Isoamericanol A and Isoamericanin A.

ChemInform ◽  
2004 ◽  
Vol 35 (38) ◽  
Author(s):  
Xiaobi Jing ◽  
Yaocheng Shi ◽  
Yonghong Liu ◽  
Ying Han ◽  
Chaoguo Yan ◽  
...  
Keyword(s):  
Bond Formation ◽  
Palladium Catalyzed ◽  
One Step

scholarly journals Understanding Bond Formation in Polar One-Step Reactions. Topological Analyses of the Reaction between Nitrones and Lithium Ynolates

2015 ◽  
Vol 80 (8) ◽  
pp. 4076-4083 ◽  
Author(s):  
David Roca-López ◽  
Victor Polo ◽  
Tomás Tejero ◽  
Pedro Merino
Keyword(s):  
Bond Formation ◽  
One Step

scholarly journals One-Step Biocatalytic Synthesis of Sustainable Surfactants Using Selective Amide Bond Formation

2021 ◽  
Author(s):  
Max Lubberink ◽  
Christian Schnepel ◽  
Christopher Baldwin ◽  
Nicholas Turner ◽  
Sabine Flitsch
Keyword(s):  
Fatty Acids ◽  
Carboxylic Acid ◽  
Enzymatic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Esterification Reaction ◽  
Amide Bond Formation ◽  
Selective Strategy ◽  
One Step ◽  
Acyl Phosphate

N-alkanoyl-N-methylglucamides (MEGAs) are non-toxic surfactants widely used in pharmaceutical and biochemical applications and hence more sustainable syntheses towards these compounds are highly desired. Here we present an aqueous, enzymatic synthesis route towards MEGAs and analogues using carboxylic acid reductase (CAR), which has been engineered to catalyse amide bond formation (CAR-A). Compared to lipase catalysed reactions, this biocatalyst is capable of selective amide bond formation between amino-polyols and fatty acids without the competing esterification reaction being observed. The wide substrate scope of CAR-A catalysed amidation was exemplified by the synthesis of 16 amides including several commercially relevant targets. The ATP co-factor could be recycled from cheap polyphosphate using a kinase. This work establishes acyl-phosphate mediated chemistry as a selective strategy for biocatalytic amide bond formation in the presence of competing alcohol functionalities.

scholarly journals An electron localization function analysis of the molecular mechanism and the C–O bond formation in the [3+2] cycloaddition reaction involving zwitterionic type between a nitrone and an electron deficient ethyne

2019 ◽  
Vol 45 ◽  
pp. 146867831982574
Author(s):  
Abdelilah Benallou ◽  
Habib El Alaoui El Abdallaoui ◽  
Hocine Garmes
Keyword(s):  
Electron Density ◽  
Function Analysis ◽  
Bond Formation ◽  
Cycloaddition Reaction ◽  
Intrinsic Reaction Coordinate ◽  
Dimethyl Acetylenedicarboxylate ◽  
Central Carbon ◽  
One Step ◽  
Free Activation Energy ◽  
Step Mechanism

The mechanistic nature of a [3+2] cycloaddition reaction involving zwitterionic species has been investigated, and the changes of electron density related to the O–C and C–C bond formation along the intrinsic reaction coordinate have been characterized. This polar [3+2] cycloaddition reaction, which takes place through a non-concerted two-stage one-step mechanism, proceeds with a moderate Gibbs free activation energy of 21 kcal mol−1. The reaction begins by the creation of a pseudoradical centre at the central carbon, first on the dimethyl acetylenedicarboxylate, and second on the nitrone framework. This immediately favours the formation of the first O–C single bond by donation of some electron density of the oxygen atom lone pairs, which represents the most attractive centre in this cycloaddition reaction.

Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres

2015 ◽  
Vol 51 (77) ◽  
pp. 14505-14508 ◽  
Author(s):  
Jola Pospech ◽  
Alastair J. J. Lennox ◽  
Matthias Beller
Keyword(s):  
Diazo Compounds ◽  
Tandem Reaction ◽  
Quaternary Carbon ◽  
One Step

An intermolecular tandem reaction for the rapid build-up of densely functionalised α-alkoxy-β-oxo-esters has been developed.

Novel N-Transfer Reagent for Converting α-Amino Acid Derivatives to α-Diazo Compounds

2021 ◽  
Author(s):  
Guan-Han Lu ◽  
Tzu-Chia Huang ◽  
Hsiao Chin Hsueh ◽  
Shin-Cherng Yang ◽  
Ting Wei Cho ◽  
...  
Keyword(s):  
Amino Acid ◽  
Diazo Compounds ◽  
Amino Acid Derivatives ◽  
N Transfer ◽  
One Step

A novel universal N-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step...

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