Palladium-Catalyzed Direct C–H Arylation of 3-Butenoic Acid Derivatives

Yang, Shan; Liu, Lingling; Zhou, Zheng; Huang, Zhibin; Zhao, Yingsheng

doi:10.1021/acs.orglett.0c03773

Cited by 17 publications

(7 citation statements)

References 33 publications

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“…13 C NMR (200 MHz, CDCl3) δ (ppm): δ 172.57 (2 CO), 172.20 (CO), 140.92 (3CH), 128.20 (6CH), 128.15 (6CH), 125.77 (3CH), 68.78 (CH), 61.91 (2CH2), 34.72 (6CH2), 33.16 (2CH2), 32.98 (4CH2), 26.16 (6 CH2). 1 H and 13 C NMR data are in agreement with those reported in the literature [15] …”

Section: Methodssupporting

confidence: 91%

“…Glycerol phenylbutyrate (6) 13 C NMR data are in agreement with those reported in the literature. [15] N,N'-Diciclohexil-N- [4-phenylbutanoil]urea: 1 H NMR (200 MHz, CDCl 3 ) δ 7.34-7.17 (5 H, m, ArCH), δ 3.92-3.81 (1H, m, CH), δ 3.72-3.58 (1H, m, CH), δ 2.72-2.65 (2H, t, CH 2 ), δ 2.46-2.38 (2H, t, CH 2 ), δ 2.07-2.00 (2H, m, CH 2 ), δ 1.96-1.08 (10CH 2 , m, CH 2 ), δ = 6.92 (NH). 13 N,N'-Diisopropryl-N- [4-phenylbutanoil]urea: 1 H NMR (200 MHz, CDCl 3 ) δ 7.32-7.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, the synthesis of GPB with a reaction yield of 80 % through a route that involves the use of carbodiimide N,N'dicyclohexylcarbodiimide (DCC) as a coupling agent in dichloromethane is reported in the literature, [15] but nothing indicates about the processes of purification and the purity achieved in the isolated product. A major drawback in the use of DCC as a coupling agent is the formation of dicyclohexylurea (DCU) which is difficult to completely eliminate and partially remains in the product [16,17] as can be seen in the 1 H NMR spectrum of GPB published in the study cited above.…”

Section: Introductionmentioning

confidence: 99%

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An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

Suchetti,

Foray,

Tempesti

et al. 2024

ChemistrySelect

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Hyperammonemia is a life‐threatening condition which can affect patients at any age. In pediatric patients, hyperammonemia can be caused by various acquired or inherited disorders such as urea cycle deficiencies or organic acidemias. Glycerol phenylbutyrate (GPB) is an orphan drug used in the treatment of hyperammonemia. GPB is a triglyceride composed of three phenylbutyric acid (PBA) molecules esterified to a glycerol molecule, which is synthesized through the acyl chloride route using thionyl chloride as an acylating agent. In this work we have developed an alternative synthesis method to obtain GPB directly under ambient conditions and avoiding the use of chlorinated solvents. Moreover, the use of carbodiimides as coupling agents, instead of thionyl chloride, allowed the conversion to the GPB in higher yields and with higher purity, without the need for column purification. We present a methodology that allows the production of GPB in a simple, efficient and environmentally and human health friendly way.

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Section: Methodssupporting

confidence: 91%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

Suchetti,

Foray,

Tempesti

et al. 2024

ChemistrySelect

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“…3 Over the past two decades, several efforts have been devoted to control the undesired chain-walking process. In particular, the palladium-catalyzed oxidative Heck reactions independently developed by Sigman, 4 White, 5 Engle, 6 and Zhao 7 emerged as an attractive strategy to access a single regioisomeric Heck product in good yield and regioselectivity (Scheme 1b). However, the requirement of a stoichiometric external oxidant and preinstalled directing/ chelating group on the alkene substrate hinders the broad applicability of this approach.…”

mentioning

confidence: 99%

Gold-Catalyzed Heck Reaction

et al. 2023

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Herein, we report a gold-catalyzed Heck reaction facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis. The elementary organometallic steps such as migratory insertion and β-hydride elimination have been realized in the catalytic fashion for the first time in gold chemistry. The present methodology not only overcomes the limitations of previously known transition metalcatalyzed Heck reactions such as the requirement of specialized substrates and formation of a mixture of regioisomeric products as a result of the undesirable chain-walking process but also offers complementary regioselectivity as compared to other transition metal catalysis.

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“…In the past few decades, unremitting efforts have been devoted to this field 11,12 . White et al pioneered a substrate-chelated oxidative Heck reaction of phenylboronic acids and unactivated alkenes tethered with proximal heteroatoms for the regioselective synthesis of vinyl products [13][14][15][16][17][18] . Shortly thereafter, the Sigman group reported a catalyst-controlled β-H elimination process in both oxidative and classic Heck reactions of unactivated alkenes, giving good selectivity for the E-styrenyl products.…”

mentioning

confidence: 99%

Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides

Zhao

Dong

et al. 2022

Nat Commun

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The control of regioselectivity in Heck-type reaction of unactivated alkenes represents a longstanding challenge due to several detachable hydrogens in β–H elimination step, which generally afford either one specific regioisomer or a mixture. Herein, a copper-catalyzed intermolecular Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides with divergent regioselectivities is reported. The complete switch of regioselectivity mainly depends on the choice of different additives. Employment of alcohol solvent gives access to vinyl products, while the addition of carboxylate leads to the formation of allylic products. In addition, exclusion of these two promoting factors results in β-lactams via a C–N reductive elimination. This protocol shows a broad substrate scope for both alkenes and structurally diverse N-fluoro-sulfonamides, producing the corresponding products with excellent regio- and stereoselectivities. Further control experiments and DFT calculations provide in-depth insights into the reaction mechanism, highlighting the distinct effect of the additives on a bidentate auxiliary-stabilized Cu(III) intermediate.

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Palladium-Catalyzed Direct C–H Arylation of 3-Butenoic Acid Derivatives

Cited by 17 publications

References 33 publications

An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

Gold-Catalyzed Heck Reaction

Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides

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