Ipso-nitration of carboxylic acids using a mixture of nitronium tetrafluoroborate, base and 1-hexyl-3,4,5-trimethyl-1H-imidazolium tetrafluoroborate

Natarajan, Palani; Chaudhary, Renu; Venugopalan, P.

doi:10.1016/j.tetlet.2019.05.057

Cited by 11 publications

(4 citation statements)

References 73 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Its synthetic utility was demonstrated by the synthesis of two drugs, fexinidazole and nitazoxanide, in good yields. The group reported an alternative protocol based on an imidazolium salt as the reaction medium in the absence of any Ag salt [334] . This metal‐free protocol shows similar substrate scope.…”

Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

View full text Add to dashboard Cite

Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

show abstract

Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…3 In general, decarboxylative nitration processes can be classified into three major groups depending on the carboxylic acid substrate, i.e., aromatic carboxylic acids, α,β-unsaturated carboxylic acids, and aliphatic carboxylic acids (Scheme 1a ). 4 The decarboxylative nitration of aromatic and α,β-unsaturated carboxylic acids by using, for example, NO 2 BF 4 /Ag 2 CO 3 , 4a Bi(NO 3 ) 3 ·5H 2 O/K 2 S 2 O 8 , 4b imidazolium nitrate salts, 4c d HNO 3 /AIBN, 4e t -BuONO/TEMPO, 4f or TMSCl–Cu(NO 3 ) 2 ·3H 2 O, 4g is well developed (Scheme 1a ; I and II). However, such transformations of aliphatic substrates are less well developed and in the only report on this type of reaction, a combination of NO 2 BF 4 and Ag 2 CO 3 in N , N -dimethylacetamide (DMA) as a solvent was used.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Phae-nok¹,

Kuhakarn²,

Leowanawat³

et al. 2022

Synlett

View full text Add to dashboard Cite

Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β position as their characteristic functionality, using a combination of AgNO3/K2S2O8 was investigated. The dual function of AgNO3 as an initiator for decarboxylation process and a nitrogen dioxide radical source that reacts with aliphatic carboxylic substrates of this study was reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41-85% yields) with moderate selectivity in one-pot operation. The reactions completed within acceptable reaction time (2 h) under mild reaction conditions that γ-butyrolactone core could be tolerated. The present study represents the direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones which are important precursors in organic transformations.

show abstract

“…The radical addition/ decarboxylation cascade could be used as an alternative protocol for the nitroolefins synthesis. Fe(NO 3 ) 3 , NaNO 3 , Bi(NO 3 ) 3 ⋅ 5H 2 O, NO 2 BF 4 , tert ‐butyl nitrite (TBN), and 1,3‐disulfonic acid imidazolium nitrate ([Dsim]NO 3 ) were used as the ⋅NO 2 precursor. For an example, in 2015, the Rajanna group described an ultrasonically assisted nitration via multicomponent reactions of trichloroisocyanuric acid, DMF, NaNO 2 and cinnamic acids.…”

Section: Radical Additionmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

View full text Add to dashboard Cite

The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

show abstract

Ipso-nitration of carboxylic acids using a mixture of nitronium tetrafluoroborate, base and 1-hexyl-3,4,5-trimethyl-1H-imidazolium tetrafluoroborate

Cited by 11 publications

References 73 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Recent Advances of Cinnamic Acids in Organic Synthesis

Contact Info

Product

Resources

About