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

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

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Publication Details

Journal
Organic Letters
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c04239
Citations
6
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
Field-Weighted Citation Impact
1.50

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article

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

Shuaijie Wu, Guodong Zhang, Chao‐Guo Yan, Wenyu Zhang et al.
6 citations
Organic Letters
Synthesis and pharmacology of benzodiazepine derivatives
1.50
article

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

Shuaijie Wu, Guodong Zhang, Chao‐Guo Yan, Wenyu Zhang, Lei Wang, Qing Wu, Ying Han
article en
6 citations

Abstract

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

Organic LettersVol. 27(1)
Yangzhou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangsu Province
Openalex Percentile: Top 18%
Synthesis and pharmacology of benzodiazepine derivatives
1.50
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Enantioselective Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction — Shuaijie Wu, Guodong Zhang, et al. · Organic Letters (2024) | TGRS Research Map | TGRS