scholarly journals Synthesis of -Tosyloxylated gem-Difluoroalkanes via Oxidative Fluorination of Vinyl Sulfonates Featuring A [2,3]-Sulfonyloxy Migration

2021 ◽  
Author(s):  
Honggen Wang ◽  
Fang-Hai Tu ◽  
Zhan Li ◽  
Shuang Yang ◽  
Yin Li ◽  
...  
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Sn2 Reactions ◽  
Modular Synthesis

The gem-difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration is involved as a key step. The OTs group in the product enables a divergent and modular synthesis of a wide variety of functionalized gem-difluoroalkanes via reliable SN2 reactions. Notable features of this protocol include mild reaction conditions, high efficiency and remarkably good functional-group tolerance.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

scholarly journals Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

2017 ◽  
Vol 13 ◽  
pp. 2610-2616 ◽  
Author(s):  
Tao Fan ◽  
Wei-Dong Meng ◽  
Xingang Zhang
Keyword(s):  
Alkyl Radical ◽  
Functional Group ◽  
High Efficiency ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Type Reaction ◽  
Alkyl Bromides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Hydroxy Groups

An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction.

scholarly journals Facile Synthesis of 2H-Benzo[h]Chromenes via an Arylamine-Catalyzed Mannich Cyclization Cascade Reaction

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3617
Author(s):  
Yueteng Zhang ◽  
Peng Ji ◽  
Xiang Meng ◽  
Feng Gao ◽  
Fanxun Zeng ◽  
...  
Keyword(s):  
Broad Spectrum ◽  
High Efficiency ◽  
Cascade Reaction ◽  
Facile Synthesis ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Notable Feature ◽  
Efficient Generation ◽  
Mannich Cyclization

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

SN2’ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

Synthesis ◽  
2021 ◽  
Author(s):  
Meng-Meng Sun ◽  
Haidong Liu ◽  
Chuan Zhu ◽  
Chao Feng
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Catalytic Amount ◽  
Synthetic Chemistry ◽  
Potential Utility ◽  
Reaction Conditions

An SN2’ defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes was reported. The reaction is triggered by catalytic amount of TBAF with the extruded fluoride in reaction serving as the sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions enable the potential utility of this method in synthetic chemistry.

Unexpected Iodine-Promoted Aerobic Oxidation of α-Cyano-δ-keto Esters: A Facile Synthesis of α,δ-Dicarbonyl Esters

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1841-1846
Author(s):  
Ze Zhang ◽  
Hui Xu ◽  
Ming-Yue Weng ◽  
Hong Chen
Keyword(s):  
High Efficiency ◽  
Aerobic Oxidation ◽  
Conjugate Addition ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Green Method ◽  
Keto Esters

An efficient and green method for the synthesis of various α,δ-dicarbonyl esters has been developed via a conjugate addition of ethyl cyanoacetates to chalcones and subsequent iodine-promoted aerobic oxidation. The present protocol features mild reaction conditions, high efficiency, easily available starting materials, and broad substrate scope.

Facile synthesis of vicinal halohydrins via organocatalytic halogen nucleophile-induced regioselective opening of epoxides

2021 ◽  
Vol 18 ◽  
Author(s):  
Niharika Sinha ◽  
Anchal Singhal ◽  
Deeksha Sharma ◽  
Shiv Murat Singh Chauhan
Keyword(s):  
Ring Opening ◽  
Functional Group ◽  
Solvent Polarity ◽  
Halide Ions ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Halide Anion ◽  
Ring Opening Of Epoxides ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Background: The calix[4]pyrrole is reported as a novel organocatalyst for regioselective ring opening of epoxides under mild reaction conditions. Methods: The reaction involves elemental halogen as a nucleophile to afford vicinal halohydrins in good to excellent yield (75-95%). Results : The reactivity of the halide anion in the reaction is governed by different factors, including solvent polarity, temperature and non-covalent interactions of the functional group present on calix[4]pyrrole moiety with halide ions. Conclusion: An efficient methodology has been developed for the regioselective synthesis of halohydrins in good to excellent yields.

Modular Synthesis of α-Substituted Alkenyl Acetals via Pd-Catalyzed Suzuki Reaction of α-Halide Alkenyl Acetals with Organoboranes

Synlett ◽  
2020 ◽  
Author(s):  
Li Zhang
Keyword(s):  
Functional Group ◽  
Suzuki Reaction ◽  
Scale Up ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Reaction Conditions ◽  
Modular Synthesis ◽  
Synthetic Strategy ◽  
High Yields

A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Halide alkenyl acetals could react smoothly with (hetero)aryl boronic acids, aryl boronates and alkyl-9-BBN via Pd-catalyzed Suzuki cross-coupling under mild reaction conditions in good to high yields. This protocol features broad substrate scope, good functional group compatibility, and easy scale-up ability.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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