KI-catalyzed α-acyloxylation of acetone with carboxylic acids

2016 ◽  
Vol 14 (25) ◽  
pp. 5936-5939 ◽  
Author(s):  
Ya-Dong Wu ◽  
Bei Huang ◽  
Yue-Xin Zhang ◽  
Xiao-Xu Wang ◽  
Jian-Jun Dai ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Present Method ◽  
Functional Group ◽  
Reaction Conditions ◽  
Aromatic Carboxylic Acids

A KI catalyzed reaction of acetone with aromatic carboxylic acids is achieved, leading to α-acyloxycarbonyl compounds in good to excellent yields under mild reaction conditions. The present method exhibits good functional-group compatibility.

Copper-Catalyzed Decarboxylation of Aromatic Carboxylic Acids: En Route to Milder Reaction Conditions

2013 ◽  
Vol 355 (4) ◽  
pp. 790-796 ◽  
Author(s):  
Gérard Cahiez ◽  
Alban Moyeux ◽  
Olivier Gager ◽  
Maël Poizat
Keyword(s):  
Carboxylic Acids ◽  
Reaction Conditions ◽  
Aromatic Carboxylic Acids

scholarly journals Triflic Anhydride Promoted Synthesis of Primary Amides and their Conversion into Nitriles

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0180-0191
Author(s):  
Anil Rana ◽  
Varun Kumar ◽  
Lata Tiwari ◽  
Anamika Thakur ◽  
Chhuttan Meena ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Reaction Conditions ◽  
One Pot ◽  
Limited Success ◽  
High Yields

A facile, two-pot conversion of carboxylic acids into the corresponding nitriles has been developed using triflic anhydride as a promoter and aqueous NH4OH as a source of nitrogen. The methodology involves synthesis of primary amides from carboxylic acids as the key first step using triflic anhydride and aqueous NH4OH as a source of ­nitrogen. Triflic anhydride is also found to be an excellent reagent for conversion of primary amides into nitriles, affording high yields with considerable chemoselectivity and functional group tolerance. In spite of the mild reaction conditions and broad substrate scope for the two-step conversions, all attempts for one-pot domino conversion of acids into nitriles exhibited limited success because of poor yields.

ChemInform Abstract: Copper-Catalyzed Decarboxylation of Aromatic Carboxylic Acids: En Route to Milder Reaction Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (30) ◽  
pp. no-no
Author(s):  
Gerard Cahiez ◽  
Alban Moyeux ◽  
Olivier Gager ◽  
Mael Poizat
Keyword(s):  
Carboxylic Acids ◽  
Reaction Conditions ◽  
Aromatic Carboxylic Acids

Synthesis of Spirofluorenyl-1,2,4-oxadiazinan-5-ones through Metal-Free [3+3] Cycloaddition of N-Vinyl Fluorenone Nitrones with Aza-oxyallyl Cations

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 424-432 ◽  
Author(s):  
Yan Luo ◽  
Chun-Hua Chen ◽  
Jin-Qi Zhang ◽  
Cui Liang ◽  
Dong-Liang Mo
Keyword(s):  
Present Method ◽  
Functional Group ◽  
Reaction Conditions ◽  
Alkyl Aryl ◽  
Metal Free ◽  
Oxyallyl Cations

Spirofluorenyl-1,2,4-oxadiazinan-5-ones are prepared in good to excellent yields through metal-free [3+3] cycloaddition of N-vinyl fluorenone nitrones and aza-oxyallyl cations under mild reaction conditions. Detailed studies reveal that N-vinyl fluorenone nitrones show greater reactivity in [3+3] cycloadditions with aza-oxyallyl cations compared to N-alkyl/aryl fluorenone nitrones. The spirofluorenyl-1,2,4-oxadiazinan-5-ones are easily prepared on gram scale. The present method features mild reaction conditions, broad substrate scope, good functional group tolerance and efficient [3+3] cycloadditions of 9-fluorenone nitrones.

Exploration of Mesyl Chloride in a One Pot Conversion of Carboxylic Acids to Ketones

2020 ◽  
Vol 7 (3) ◽  
pp. 242-247
Author(s):  
Habtamu Gelaw Mekonnen ◽  
Debasis Sahoo ◽  
Samaresh Jana ◽  
Sanjoy Kumar Maji
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Functional Group ◽  
Reaction Times ◽  
Mixed Anhydride ◽  
Organometallic Reagent ◽  
Reaction Conditions ◽  
One Pot ◽  
Organometallic Reagents ◽  
Organolithium Reagents

Background: Due to the ubiquitous nature of the ketone functionality, it is considered an important functional group in organic chemistry. Hence, the synthesis of ketones from readily available starting materials is an important chemical transformation in organic synthesis. Consequently, several research efforts have been reported in the literature for the transformation of carboxylic acids to ketones in a one-pot synthesis. However, some of the procedures have limitations, such as long reaction times, harsh reaction conditions, and usage of expensive metal catalysts. Thus, a simple and convenient one-pot conversion of carboxylic acids to ketones remains desirable. Objective: We intended to develop a simple and convenient one-pot methodology for the synthesis of ketones from carboxylic acids. Our objective was to build up a carboxylic acid-based chemical template where various types of organometallic reagents can interact to produce the desired ketone. Methods: In this procedure, a carboxylic acid was converted to a mixed anhydride using mesyl chloride in the presence of a base. This mixed anhydride was then reacted with a suitable organometallic reagent at -20°C to obtain the desired ketone. The reaction was performed in a one-pot fashion. Results: Under the optimized reaction conditions, various aromatic and heteroaromatic carboxylic acids were converted to the corresponding ketones using organolithium and organomagnesium reagents with short reaction times. Moderate to good yields of the desired ketones were observed in many of these transformations. Conclusion: A simple and convenient one-pot method for the conversion of carboxylic acids to ketones has been reported. Specifically, various aromatic and `heteroaromatic carboxylic acids have been converted to the corresponding ketones in moderate to good yields. Organomagnesium and organolithium reagents were used as nucleophiles for this reaction.

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

2020 ◽  
Vol 56 (29) ◽  
pp. 4067-4069 ◽  
Author(s):  
Ya-Nan Wu ◽  
Ming-Chen Fu ◽  
Rui Shang ◽  
Yao Fu
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aromatic Carboxylic Acids ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Lithium Formate

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions.

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.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

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