Preparation of 3-O-aryl chloramphenicol derivatives via chemoselective copper-catalyzed O-arylation of (1R,2R)-(−)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuthines

Ahmad, Tabinda; Dansereau, Julien; Hébert, Martin; Grand‐Maître, Chantal; Larivée, Alexandre; Siddiqui, A. M.; Gagnon, Alexandre

doi:10.1016/j.tetlet.2016.08.021

Cited by 13 publications

(7 citation statements)

References 74 publications

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“…Due to the borderline behavior of bismuth as a metal and a ligand, organobismuth species have been used as reagents and catalysts in a wide range of reactions. We reported a portfolio of methods for the construction of C–C [26–29], C–N [30] and C–O bonds [31–33] using triaryl- and trialkylbismuthines [34]. We also disclosed for the first time in 2007 the synthesis of tricyclopropylbismuth ( 24 ) and its use in N-cyclopropylation [35], palladium-catalyzed cross coupling [36] and carbonylative cross-coupling reactions [37].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Benoit¹,

Fnaiche²,

Gagnon³

2019

Beilstein J. Org. Chem.

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The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.

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Section: Introductionmentioning

confidence: 99%

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Benoit¹,

Fnaiche²,

Gagnon³

2019

Beilstein J. Org. Chem.

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“…The chemioselective copper catalyst was developed for the O-arylation of (1R,2R)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediols using triarylbis-muth, where BOC is tert-butoxycarbonyl group (Scheme 24). The method makes it possible to transfer ortho-, meta-, and para-substituted aryl groups, is highly tolerant to functional groups, and leads to the arylation of primary alcohols [29].…”

Section: Scheme 22mentioning

confidence: 99%

Organic Compounds of Bismuth: Synthesis, Structure, and Applications

2021

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“…We recently reported the copper-catalyzed arylation of N-Boc chloramphenicol derivatives using triarylbismuthines (Scheme 25). 198 Twelve derivatives were prepared using functionalized triarylbismuthines. The N-Boc arylated products were converted into the corresponding 3-O-arylchloramphenicol derivatives by treatment with TFA and reaction with methyl dichloroacetate.…”

Section: Syn Thesismentioning

confidence: 99%

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

2017

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Organobismuth compounds are organometallic reagents that contain a C-Bi bond. These species, which are easily accessed from inexpensive and low-toxicity inorganic bismuth salts, are highly attractive in synthesis due to their unique properties and reactivity. A wide diversity of geometries have been found for organobismuth compounds, depending on the oxidation state of the bismuth, its charge, and the number of coordinated elements. Compounds where the bismuth bears a-1 charge (organobismuthate), a +1 (bismuthonium cation) and a +2 charge (bismuthonium dication) have been reported. Due to the presence of a lone pair, trivalent organobismuthines can act as Lewis bases in transition-metal complexes. In addition, organobismuth compounds can act as Lewis acids by forming hypervalent interactions with ligands and metals. Organobismuth compounds have been used as catalysts and reagents in a plethora of reactions. In this review, the synthesis and properties of organobismuth reagents and their use in organic reactions are reviewed. 1 Introduction 2 Synthesis of Trivalent Organobismuthines 3 Synthesis of Pentavalent Organobismuth Compounds 4 Structure, Hypervalency and Chirality 5 C-, N-, Oand S-Arylation Reactions 6 Palladium-Catalyzed Reactions 7 Other Reactions Involving Organobismuth Reagents 8 Conclusion

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Preparation of 3-O-aryl chloramphenicol derivatives via chemoselective copper-catalyzed O-arylation of (1R,2R)-(−)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuthines

Cited by 13 publications

References 74 publications

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Organic Compounds of Bismuth: Synthesis, Structure, and Applications

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

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