Selective Conversion of Furoic Acid Derivatives to Multi‐Substituted Furanacrylate by a Ruthenium Catalyst

Li, Feng; Li, Xinglong; Gong, Tian‐Jun; Fu, Yao

doi:10.1002/cctc.201901365

Cited by 12 publications

(14 citation statements)

References 95 publications

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“…With ethylene as a dienophile, this reaction results in formation of functional para ‐xylene derivatives 11 produced by deoxygenation of the Diels‐Alder adducts [41] . A recently published Ru‐catalyzed alkenylation of HMFCA with acrylates proceeds with or without decarboxylation (depending on the reaction temperature) to afford product 12 or 13 , respectively [42] …”

Section: Ab‐type Furanic Building Blocksmentioning

confidence: 99%

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

Galkin

Ananikov

2020

ChemistryOpen

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Recent decades have been marked by enormous progress in the field of synthesis and chemistry of 5‐(hydroxymethyl)furfural (HMF), an important platform chemical widely recognized as the “sleeping giant” of sustainable chemistry. This multifunctional furanic compound is viewed as a strong link for the transition from the current fossil‐based industry to a sustainable one. However, the low chemical stability of HMF significantly undermines its synthetic potential. A possible solution to this problem is synthetic diversification of HMF by modifying it into more stable multifunctional building blocks for further synthetic purposes.

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Section: Ab‐type Furanic Building Blocksmentioning

confidence: 99%

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

Galkin

Ananikov

2020

ChemistryOpen

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“…[ 15 ] In their studies towards the carboxylate‐directed olefination as well as olefination/decarboxylation of furoic acid derivatives, Fu and co‐workers showed the selective C2 functionalization of a furan bearing a carboxylic acid group at the 3‐position. [ 16 ] Interestingly, a difunctionalization of the C2‐ as well as the C4‐position occurred upon an increase of the reaction temperature required for the subsequent decarboxylation. It is worthwhile to point out that the furans were used as the limiting reagents in all of these directed methods.…”

Section: C2‐olefination Of 3‐substituted Five‐membered Heteroarenesmentioning

confidence: 99%

Regioselective Olefination of 3‐Substituted Five‐Membered Heteroarenes

2020

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Five‐membered heteroarenes constitute ubiquitous moieties in bioactive compounds and materials. It is thus not surprising that a direct and selective access to multiply substituted heteroarenes is considered as a highly attractive synthetic target. The direct olefination of such substrates, also known as cross‐dehydrogenative coupling has raised significant interest in this context. However, achieving site‐selectivity remains challenging with some substitution patterns such as 3‐substituted heteroarenes. Suitable catalyst systems and reaction conditions have to be identified, which enable the differentiation between the competing C2‐ and C5‐position. Over the last few years, substantial progress has been made to overcome this selectivity challenge mainly based on the use of novel ligand systems, which will be described herein.

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“…Another interesting example on C−H functionalization of carboxyl‐group‐containing FPC was reported in 2019 by Fu and co‐workers and was devoted to vinylation of FDCA derivatives [40] . Usage of described technique allows to obtain products of both non‐decarboxylative and decarboxylative alkenylation 30 – 33 and 34 – 40 , respectively, depending on the reaction conditions (Scheme 7).…”

Section: Functionalization Via Directing Group Strategymentioning

confidence: 99%

“… Ru‐catalyzed copper(II)‐promoted non‐decarboxylative and decarboxylative alkenylation of carboxyl‐group‐containing FPC [40] …”

Section: Functionalization Via Directing Group Strategymentioning

confidence: 99%

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Catalytic C−H Functionalization of Unreactive Furan Cores in Bio‐Derived Platform Chemicals

Karlinskii

Ananikov

2020

ChemSusChem

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C−H functionalization is one of the most convenient and powerful tools in the arsenal of modern chemistry, deservedly nominated as the “Holy Grail” of organic synthesis. A frequent disadvantage of this method is the need for harsh reaction conditions to carry out transformations of inert C−H bonds, which limits the possibility of its use for modifying less stable substrates. Biomass‐derived furan platform chemicals, which have a relatively unstable aromatic furan core and highly reactive side chain substituents, are extremely promising and valuable organic molecules that are currently widely used in a variety of research and industrial fields. The high sensitivity of furan derivatives to acids, strong oxidants, and high temperatures significantly limits the use of classical methods of C−H functionalization for their modification. New methods of catalytic functionalization of non‐reactive furan cores are urgently required to obtain a new generation of materials with controlled properties and potentially bioactive substances.

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Selective Conversion of Furoic Acid Derivatives to Multi‐Substituted Furanacrylate by a Ruthenium Catalyst

Cited by 12 publications

References 95 publications

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

Regioselective Olefination of 3‐Substituted Five‐Membered Heteroarenes

Catalytic C−H Functionalization of Unreactive Furan Cores in Bio‐Derived Platform Chemicals

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