Enantioselective Synthesis of Isoindolinone by Sequential\nPalladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction

We\npresent a tandem aza-Heck/Suzuki cross-coupling reaction of <i>O</i>-phenyl hydroxamic ethers with readily available arylboronic\nand alkenyl boronic acids. This protocol is enabled by a palladium\ncatalyst paired with chiral phosphoramidite ligands, particularly\nunder mild reaction conditions, yielding efficient and succinct synthetic\nroutes to chiral isoindolinones with high enantioselectivity. Furthermore,\nthis reaction exhibits excellent functional group compatibility and\na rich diversity of subsequent transformations.

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c04239.s001
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
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article

Enantioselective Synthesis of Isoindolinone by Sequential\nPalladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction

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Synthesis and pharmacology of benzodiazepine derivatives
article

Enantioselective Synthesis of Isoindolinone by Sequential\nPalladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction

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Abstract

We\npresent a tandem aza-Heck/Suzuki cross-coupling reaction of <i>O</i>-phenyl hydroxamic ethers with readily available arylboronic\nand alkenyl boronic acids. This protocol is enabled by a palladium\ncatalyst paired with chiral phosphoramidite ligands, particularly\nunder mild reaction conditions, yielding efficient and succinct synthetic\nroutes to chiral isoindolinones with high enantioselectivity. Furthermore,\nthis reaction exhibits excellent functional group compatibility and\na rich diversity of subsequent transformations.

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Openalex Percentile: Top 73%
Synthesis and pharmacology of benzodiazepine derivatives
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Enantioselective Synthesis of Isoindolinone by Sequential\nPalladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction · Figshare (2024) | TGRS Research Map | TGRS