Heterogeneous Direct Acylation Strategy to Diaryl Ketones and Their Application to 1, 3‐Dihydroisobenzofurans

2020 ◽  
Vol 5 (4) ◽  
pp. 1349-1352
Author(s):  
Trisha Bhattacharya ◽  
Basuli Suchand ◽  
Chinnabattigalla Sreenivasulu ◽  
Bhairi Lakshminarayana ◽  
Ch. Subrahmanyam ◽  
...  
Keyword(s):  
Direct Acylation

scholarly journals A novel pathway for lipid biosynthesis: the direct acylation of glycerol

2001 ◽  
Vol 42 (12) ◽  
pp. 1979-1986
Author(s):  
Douglas P. Lee ◽  
Andrew S. Deonarine ◽  
Martin Kienetz ◽  
Quansheng Zhu ◽  
Monika Skrzypczak ◽  
...  
Keyword(s):  
Lipid Biosynthesis ◽  
Direct Acylation

Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups

2016 ◽  
Vol 94 (1) ◽  
pp. 44-49 ◽  
Author(s):  
Toshifumi Miyazawa ◽  
Manabu Hamada ◽  
Ryohei Morimoto
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase B ◽  
Candida Antarctica Lipase ◽  
Primary Alcohols ◽  
Lipase B ◽  
Highly Active ◽  
Direct Acylation ◽  
Acyl Acceptors ◽  
Hydroxy Groups ◽  
Phenolic Hydroxy

Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.

Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 769-779 ◽  
Author(s):  
Gedu Satyanarayana ◽  
Basuli Suchand
Keyword(s):  
Acylation Reaction ◽  
One Pot ◽  
Palladium Catalyzed ◽  
Direct Acylation

A bis-acylation strategy to access functionalized anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel–Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation.

scholarly journals Direct carbon-carbon coupling of furanics with acetic acid over Brønsted zeolites

2016 ◽  
Vol 2 (9) ◽  
pp. e1601072 ◽  
Author(s):  
Abhishek Gumidyala ◽  
Bin Wang ◽  
Steven Crossley
Keyword(s):  
Acetic Acid ◽  
Density Functional ◽  
Reaction Rate ◽  
Activation Barrier ◽  
Density Functional Theory Calculations ◽  
Step Change ◽  
Functional Theory ◽  
Transportation Fuels ◽  
Bond Forming ◽  
Direct Acylation

Effective carbon-carbon coupling of acetic acid to form larger products while minimizing CO2emissions is critical to achieving a step change in efficiency for the production of transportation fuels from sustainable biomass. We report the direct acylation of methylfuran with acetic acid in the presence of water, all of which can be readily produced from biomass. This direct coupling limits unwanted polymerization of furanics while producing acetyl methylfuran. Reaction kinetics and density functional theory calculations illustrate that the calculated apparent barrier for the dehydration of the acid to form surface acyl species is similar to the experimentally measured barrier, implying that this step plays a significant role in determining the net reaction rate. Water inhibits the overall rate, but selectivity to acylated products is not affected. We show that furanic species effectively stabilize the charge of the transition state, therefore lowering the overall activation barrier. These results demonstrate a promising new route to C–C bond–forming reactions for the production of higher-value products from biomass.

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