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Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation

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Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation. / Sweeney, J.B.; Doulcet, J.; Thapa, B.

In: iScience, Vol. 9, 30.11.2018, p. 328-336.

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Sweeney JB, Doulcet J, Thapa B. Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation. iScience. 2018 Nov 30;9:328-336. Epub 2018 Nov 1. doi: 10.1016/j.isci.2018.10.025

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@article{09356f9e28d6401990264855006e8482,
title = "Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation",
abstract = "Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors. Chemistry; Catalysis; Organic Synthesis {\textcopyright} 2018 The Authors",
keywords = "Catalysis, Chemistry, Organic Synthesis",
author = "J.B. Sweeney and J. Doulcet and B. Thapa",
year = "2018",
month = nov,
day = "30",
doi = "10.1016/j.isci.2018.10.025",
language = "English",
volume = "9",
pages = "328--336",
journal = "iScience",
issn = "2589-0042",
publisher = "Elsevier Inc.",

}

RIS

TY - JOUR

T1 - Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation

AU - Sweeney, J.B.

AU - Doulcet, J.

AU - Thapa, B.

PY - 2018/11/30

Y1 - 2018/11/30

N2 - Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors. Chemistry; Catalysis; Organic Synthesis © 2018 The Authors

AB - Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors. Chemistry; Catalysis; Organic Synthesis © 2018 The Authors

KW - Catalysis

KW - Chemistry

KW - Organic Synthesis

U2 - 10.1016/j.isci.2018.10.025

DO - 10.1016/j.isci.2018.10.025

M3 - Journal article

VL - 9

SP - 328

EP - 336

JO - iScience

JF - iScience

SN - 2589-0042

ER -