A convenient procedure for the esterification of benzoic acids with phenols: a new application for the Mitsunobu reaction

Fitzjarrald, Victor P.; Pongdee, Rongson

doi:10.1016/j.tetlet.2007.03.095

Cited by 33 publications

(17 citation statements)

References 26 publications

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“…After the reaction, an aliquot of the reaction mixture was subjected to GC and GC‐MS analysis for determination of yield and conversion. All new compounds (Table 2, entries 15, 18, and 20) were characterized by 1 H and 13 C NMR spectroscopy, IR, and high‐resolution MS. All other products have already been reported in the literature (Table 2, entries 1,4b 2,16a 3,16b 4,16a 5,4b 6,16c 7,16b 8,4b 9,16d 10,16e 11,16f 12,16g 13,16h 14,16i 16,16h 17,16h 19,16h and 2116j).…”

Section: Methodsmentioning

confidence: 85%

Convenient Carbonylation of Aryl Bromides with Phenols to Form Aryl Esters by Applying a Palladium/Di‐1‐adamantyl‐n‐butylphosphine Catalyst

Neumann

Beller

2010

ChemCatChem

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Section: Methodsmentioning

confidence: 85%

Convenient Carbonylation of Aryl Bromides with Phenols to Form Aryl Esters by Applying a Palladium/Di‐1‐adamantyl‐n‐butylphosphine Catalyst

Neumann

Beller

2010

ChemCatChem

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“…Previously, our group disclosed the application of the Mitsunobu reaction for the efficient construction of arylbenzoates involving benzoic acids and phenols. 3 Within that context, we also postulated that our methodology proceeded through a non-classical mechanism, involving an acyloxyphosphonium ion rather than the more traditional alkoxyphosphonium ion, that would allow for the introduction of various nucleophiles other than substituted phenols within a similar framework. 4 As such, we elected to explore the feasibility of preparing N,N -diethylbenzamides as an extension of our Mitsunobu methodology.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N,N-Diethylbenzamides via a Nonclassical Mitsunobu Reaction

Hoffman

Miller

Gardner

et al. 2014

Synthetic Communications

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The use of the Mitsunobu reaction for the synthesis of N,N-diethylbenzamides affords ortho-, meta-, and para-substituted benzamides, containing both electron-donating and electron-withdrawing groups. While the preparation of numerous functional groups has been efficiently demonstrated employing the Mitsunobu reaction, our methodology represents the first application of the Mitsunobu reaction for the construction of benzamides using benzoic acid and amine starting materials. Moreover, this synthetic transformation is believed to proceed via a non-classical mechanism involving the existence of an acyloxyphosphonium ion.

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“…The desired phenyl ester formation, however, could be achieved under Mitsunobu conditions (PPh 3 , PhOH, DIAD, 78% yield). [16] The need to install an electron-withdrawing—and ideally easily removable—group at the isoxazole methyl group was predicated on model systems of the AB-ring system; such a group was found to be required to facilitate a conjugate addition later. To this end, deprotonation of the methyl group of phenyl ester 18 (LiHMDS) and quenching of the resulting anionic species with TeocCl produced the desired fragment 8 (86% yield).…”

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confidence: 99%