2021
DOI: 10.1021/acs.joc.1c02251
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Synthesis of Azidoanilines by the Buchwald–Hartwig Amination

Abstract: We report a Buchwald–Hartwig amination compatible with azido functionality. Treatment of azidoaryl iodides and amines with fourth-generation Buchwald precatalyst coordinated by CPhos and sodium tert-butoxide in 1,4-dioxane at 50 °C afforded the corresponding azidoanilines while leaving the azido groups intact. The method showed a broad substrate scope and was applicable to the synthesis of diazido compounds as photoaffinity probe candidates of pharmaceutical amines and multiazido platform molecules.

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Cited by 4 publications
(4 citation statements)
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“…More challenging and sterically demanding bulky aniline derivatives afforded moderate to good yields (Figure 10, entries 2f, 2g, 2j and 2m). These outcomes illustrate the excellent catalytic efficiency of Pd/ 4 system in the amination process of aryl chlorides, which is equivalent to or superior to the efficiency of catalysts observed with other phosphine‐based systems previously described [57,59–63] . Sterically demanding and electron‐rich ligands are more effective for this coupling process.…”
Section: Resultssupporting
confidence: 61%
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“…More challenging and sterically demanding bulky aniline derivatives afforded moderate to good yields (Figure 10, entries 2f, 2g, 2j and 2m). These outcomes illustrate the excellent catalytic efficiency of Pd/ 4 system in the amination process of aryl chlorides, which is equivalent to or superior to the efficiency of catalysts observed with other phosphine‐based systems previously described [57,59–63] . Sterically demanding and electron‐rich ligands are more effective for this coupling process.…”
Section: Resultssupporting
confidence: 61%
“…These outcomes illustrate the excellent catalytic efficiency of Pd/4 system in the amination process of aryl chlorides, which is equivalent to or superior to the efficiency of catalysts observed with other phosphine-based systems previously described. [57,[59][60][61][62][63] Sterically demanding and electron-rich ligands are more effective for this coupling process. Mercury drop experiment was carried out to assess the homogeneous nature of the catalysis.…”
Section: Pd Catalyzed Suzuki Reaction Between Aryl Chlorides With Phe...mentioning
confidence: 99%
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“…1A). 5,6 We found that each type of azide reacted predominantly in high selectivity with dibenzocyclooctyne derivatives, 1,3-dicarbonyl compounds under basic conditions, and terminal alkynes using a ruthenium catalyst, respectively. This enabled the facile synthesis of tri- or tetrafunctionalized molecules from multiazido platform molecules via three or four sequential triazole formations.…”
mentioning
confidence: 94%