ChemInform Abstract: DBU Catalysis of N,N′‐Carbonyldiimidazole‐Mediated Amidations.

Larrivée-Aboussafy, Claude; Jones, Brian P.; Price, Kristin E.; Hardink, Mark; McLaughlin, Robert W.; Lillie, Brett M.; Hawkins, Joel M.; Vaidyanathan, Rajappa

doi:10.1002/chin.201023071

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Table 1 Optimization Of the Amidation For The ...1

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2022

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“…Besides 2-hydroxy-5-nitropyridine, we also utilized DBU (0.5 equivalents) to facilitate the amidation (Table 1 , entry 3). 7 After 7 hours, the product 1 was isolated in 68% yield. When imidazole hydrochloride (Im·HCl) (1.5 equivalents) was employed as reported, 8 a thick paste was observed that was difficult to agitate before the mixture was heated to 82 °C.…”

Section: Table 1 Optimization Of the Amidation For The ...mentioning

confidence: 99%

An Improved Scalable Process for the Synthesis of (S,S)-DACH-Ph Trost Ligand

Zhang¹,

Chong²,

White³

et al. 2022

Synlett

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An improved chemical process has been developed for the synthesis of (S,S)-DACH-Ph Trost ligand. The amidation of 2-diphenylphosphinylbenzoic acid and (S,S)-diaminocyclohexane is promoted by stoichiometric CDI and catalytic imidazole hydrochloride. The resulting product, (S,S)-DACH-Ph Trost ligand, is isolated as a white solid in 80% yield with >99% ee by simple filtration without column chromatography. The current facile process is also demonstrated on kilogram scale.

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Section: Table 1 Optimization Of the Amidation For The ...mentioning

confidence: 99%