scholarly journals One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate

2014 ◽  
Vol 16 (4) ◽  
pp. 2111-2116 ◽  
Author(s):  
Jennifer J. Lee ◽  
George A. Kraus
Keyword(s):  
Aromatic Compounds ◽  
Terephthalic Acid ◽  
One Pot ◽  
Formal Synthesis ◽  
Methyl Pyruvate

Diverse functionalized aromatic compounds including DMT are constructed from captodative dienophiles with exclusive regioselectivity.

scholarly journals Unsymmetrical Difunctionalization of Two Different C–H Bonds in One Pot Under Transition-Metal Catalysis

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 40-54 ◽  
Author(s):  
Masahito Murai ◽  
Kazuhiko Takai
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Aromatic Compounds ◽  
Transition Metal Catalysis ◽  
One Pot ◽  
Metal Catalysis ◽  
Selective Functionalization ◽  
Sequential Addition ◽  
Target Molecules ◽  
Directing Group

Recent advancements in unsymmetrical difunctionalization based on the substitution of two different C–H bonds in one-pot are described. Due to the difficulty of controlling reactivity and selectivity, multi-functionalization via substitution of several C–H bonds to install different functional groups has been limited until recently, in comparison with well-studied functionalization via sequential addition to unsaturated π-bonds. This difunctionalization protocol provides an efficient and rapid approach to a library of structurally complicated target molecules through the formation of multiple C–X bonds with high atom- and step-economy.1 Introduction2 ortho-Selective Functionalization of Two Different C–H Bonds Relative to the Directing Group2.1 Unsymmetrical Difunctionalization with the Introduction of Similar Functional Groups2.2 Unsymmetrical Difunctionalization with the Introduction of Different Functional Groups2.3 ortho-Selective Unsymmetrical Difunctionalization Promoted by Two Different Directing Groups Appearing During the Progress of the Reaction3 ortho/meta-Selective C–H Bond Difunctionalization Relative to the Directing Group4 Sequential Difunctionalization of Fused Aromatic Compounds and Heterocycles5 Summary and Outlook

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

scholarly journals Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules

2016 ◽  
Vol 358 (10) ◽  
pp. 1602-1607 ◽  
Author(s):  
Wusheng Guo ◽  
Victor Laserna ◽  
Jeroen Rintjema ◽  
Arjan W. Kleij
Keyword(s):  
One Pot ◽  
Formal Synthesis

scholarly journals Recent Advances in Microbial Production of cis,cis-Muconic Acid

Biomolecules ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1238 ◽  
Author(s):  
Sisun Choi ◽  
Han-Na Lee ◽  
Eunhwi Park ◽  
Sang-Jong Lee ◽  
Eung-Soo Kim
Keyword(s):  
Metabolic Pathway ◽  
Aromatic Compounds ◽  
Terephthalic Acid ◽  
De Novo ◽  
Vital Role ◽  
Chemical Processes ◽  
Muconic Acid ◽  
Production Strategies ◽  
Culture Process ◽  
Foreign Genes

cis,cis-Muconic acid (MA) is a valuable C6 dicarboxylic acid platform chemical that is used as a starting material for the production of various valuable polymers and drugs, including adipic acid and terephthalic acid. As an alternative to traditional chemical processes, bio-based MA production has progressed to the establishment of de novo MA pathways in several microorganisms, such as Escherichia coli, Corynebacterium glutamicum, Pseudomonas putida, and Saccharomyces cerevisiae. Redesign of the metabolic pathway, intermediate flux control, and culture process optimization were all pursued to maximize the microbial MA production yield. Recently, MA production from biomass, such as the aromatic polymer lignin, has also attracted attention from researchers focusing on microbes that are tolerant to aromatic compounds. This paper summarizes recent microbial MA production strategies that involve engineering the metabolic pathway genes as well as the heterologous expression of some foreign genes involved in MA biosynthesis. Microbial MA production will continue to play a vital role in the field of bio-refineries and a feasible way to complement various petrochemical-based chemical processes.

Synthesis of Fluorinated Aromatic Compounds by One-Pot Benzyne Generation and Nucleophilic Fluorination

2014 ◽  
Vol 67 (3) ◽  
pp. 475 ◽  
Author(s):  
Takashi Ikawa ◽  
Shigeaki Masuda ◽  
Tsuyoshi Nishiyama ◽  
Akira Takagi ◽  
Shuji Akai
Keyword(s):  
Aromatic Compounds ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Fluoride Ions ◽  
One Pot ◽  
Substituted Benzenes ◽  
Fluorinated Aromatic Compounds ◽  
Nucleophilic Fluorination ◽  
Sequential Reactions

The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential reactions in one-pot: the nonaflylation of phenols, benzyne generation, and nucleophilic fluorination of the benzynes. The regioselectivities of these reactions are controlled by the substituents at the C3-position of the benzynes.

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