Electrophilic activation of aminocarboxylic acid by phosphate ester promotes Friedel–Crafts acylation by overcoming charge–charge repulsion

2017 ◽  
Vol 15 (44) ◽  
pp. 9398-9407 ◽  
Author(s):  
Akinari Sumita ◽  
Yuko Otani ◽  
Tomohiko Ohwada
Keyword(s):  
Conformational Change ◽  
Carboxylic Acids ◽  
Phosphate Ester ◽  
Aromatic Ketones ◽  
Aminocarboxylic Acid ◽  
Electrophilic Activation ◽  
Acyl Phosphate

o-Methyl salicylates enhance the reactivity of the phosphate ester via a protonation-induced conformational change to generate acyl phosphate, thereby overwhelming the charge–charge repulsion associated with formation of the acylium ion, enabling aromatic ketones to be generated from various carboxylic acids.

Chemoselective generation of acyl phosphates, acylium ion equivalents, from carboxylic acids and an organophosphate ester in the presence of a Brønsted acid

2017 ◽  
Vol 53 (9) ◽  
pp. 1482-1485 ◽  
Author(s):  
Akinari Sumita ◽  
Yuko Otani ◽  
Tomohiko Ohwada
Keyword(s):  
Carboxylic Acids ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Aromatic Ketones ◽  
Brönsted Acid ◽  
Acyl Phosphate

Reactions of an organophosphate ester with carboxylic acids proceeded smoothly and chemoselectively in the presence of a Brønsted acid, affording acyl phosphate intermediates, leading to formation of various functional aromatic ketones.

Bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with O2 under metal- and base-free conditions

2018 ◽  
Vol 20 (13) ◽  
pp. 3038-3043 ◽  
Author(s):  
Kai-Jian Liu ◽  
Si Jiang ◽  
Ling-Hui Lu ◽  
Ling-Li Tang ◽  
Shan-Shan Tang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Metal Base ◽  
Aromatic Ketones ◽  
Aromatic Carboxylic Acids ◽  
Oxidation Of Alcohols ◽  
Aromatic Alcohols

A practical and eco-friendly protocol for the oxidation of alcohols into carboxylic acids and ketones under metal-, base- and additive-free conditions is reported.

Sythesis of aromatic ketones from carboxylic acids and phenyllithium. Destruction of the excess phenyllithium

1981 ◽  
Vol 46 (19) ◽  
pp. 3928-3929 ◽  
Author(s):  
David E. Nicodem ◽  
M. L. P. F. C. Marchiori
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Ketones

Asymmetric reduction of prochiral aromatic ketones with modified reagents prepared from sodium borohydride and carboxylic acids in the presence of 1,2:5,6-di-O-isopropylidene-.alpha.-D-glucofuranose

1980 ◽  
Vol 45 (21) ◽  
pp. 4231-4233 ◽  
Author(s):  
Akira Hirao ◽  
Seiichi Nakahama ◽  
Hidenori Mochizuki ◽  
Shinichi Itsuno ◽  
Noboru Yamazaki
Keyword(s):  
Carboxylic Acids ◽  
Sodium Borohydride ◽  
Asymmetric Reduction ◽  
Aromatic Ketones

Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium

2014 ◽  
Vol 12 (48) ◽  
pp. 9760-9763 ◽  
Author(s):  
Mohan Pal ◽  
Stephen L. Bearne
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Coenzyme A ◽  
Aromatic Carboxylic Acids ◽  
Phosphate Monoesters ◽  
Aqueous Conditions ◽  
Acyl Phosphate

Regioselective S-acylation of coenzyme A is achieved under aqueous conditions using various aliphatic and aromatic carboxylic acids activated as their methyl acyl phosphate monoesters.

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds

2020 ◽  
Vol 22 (13) ◽  
pp. 4357-4363 ◽  
Author(s):  
Xianjin Zhu ◽  
Yong Liu ◽  
Can Liu ◽  
Haijun Yang ◽  
Hua Fu
Keyword(s):  
Carboxylic Acids ◽  
Selective Oxidation ◽  
Value Added ◽  
Aromatic Ketones

A light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds has been developed. High-value-added aromatic ketones and carboxylic acids were easily prepared in high-to-excellent yields using readily available starting materials.

“One-Pot” Synthesis of γ-Pyrones from Aromatic Ketones/Heteroarenes and Carboxylic Acids

2020 ◽  
Vol 85 (23) ◽  
pp. 15051-15061
Author(s):  
Xiangyu Sun ◽  
Ming Gong ◽  
Mengmeng Huang ◽  
Yabo Li ◽  
Jung Keun Kim ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
One Pot ◽  
Aromatic Ketones ◽  
One Pot Synthesis

scholarly journals A NEW METHOD FOR THE PREPARATION OF SYMMETRICAL AROMATIC KETONES FROM AROMATIC CARBOXYLIC ACIDS

1980 ◽  
Vol 9 (1) ◽  
pp. 51-52 ◽  
Author(s):  
Toshio Goto ◽  
Makoto Onaka ◽  
Teruaki Mukaiyama
Keyword(s):  
Carboxylic Acids ◽  
New Method ◽  
Aromatic Ketones ◽  
Aromatic Carboxylic Acids
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