Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N

Phakhodee, Wong; Duangkamol, Chuthamat; Wangngae, Sirilak; Pattarawarapan, Mookda

doi:10.1016/j.tetlet.2015.12.009

Cited by 19 publications

(11 citation statements)

References 41 publications

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“…Compound 3d (624 mg, 44%) was obtained as a white solid: mp 70–72 °C; 1 H NMR (600 MHz, CDCl 3 ) δ 8.03 (dt, J = 8.0, 1.1 Hz, 1H, Ar), 7.56–7.50 (m, 2H, Ar), 7.43–7.37 (m, 1H, Ar) ppm; 13 C{ 1 H} NMR (151 MHz, CDCl 3 ) δ 160.53, 135.28, 134.33, 132.75, 131.81, 128.07, 127.08 ppm; HRMS (EI) m / z [M – Cl] + calcd for C 14 H 8 O 3 Cl 259.0162, found 259.0157. The 1 H NMR spectrum is in full agreement with that reported in literature …”

Section: Methodssupporting

confidence: 90%

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Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

2021

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Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.

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Section: Methodssupporting

confidence: 90%

“…The 1 H NMR spectrum is in full agreement with that reported in literature. 27 2-Bromobenzoic Anhydride 3e. 2-Bromobenzoic acid (2.00 g, 9.85 mmol, 1.0 equiv), TsCl (938 mg, 4.93 mmol, 0.5 equiv), and K 2 CO 3 (2.04 g, 4.93 mmol, 1.5 equiv) were dissolved in MeCN (50 mL) and CH 2 Cl 2 (50 mL) and synthesized according to GP A.…”

Section: ■ Conclusionmentioning

confidence: 99%

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

2021

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“…In addition to benzoic anhydride, other monoanhydrides were prepared according to previously reported methods . Reactants and reagents were purchased from commercial suppliers and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Forging C–S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation

et al. 2019

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A nickel-catalyzed decarbonylation or decarbonylation accompanied by decarboxylation cross-coupling reaction of aryl anhydrides with thiophenols as coupling partners was disclosed. This method is promoted by a commercially available, moisture-stable, and inexpensive nickel(II) precatalyst. The process can tolerate a variety of functional groups using ubiquitous aryl anhydrides as cross-coupling precursors to produce thioethers in moderate to excellent yields.

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“…All chemicals were of reagent grade quality obtained from commercial sources and used as received. Benzoic anhydrides 2 19 and benzoxazoles 3 20 were prepared according to the literature. General Procedure for Synthesis of 4−7.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[d]oxazoles

et al. 2018

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We report an efficient palladium-catalyzed approach to the synthesis of benzoxazole derivatives via sequential heteroarylation/acylation reaction of iodobenzenes. Three readily available starting materials, iodobenzenes, anhydrides, and benzoxazoles, were smoothly coupled to form new C-C bonds at the ortho and ipso positions of the iodobenzenes to afford 2-heteroaryl-3-acylbenzene derivatives in good yields.

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Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N

Cited by 19 publications

References 41 publications

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Forging C–S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation

Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[d]oxazoles

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