Precision Propargylic\nSubstitution Reaction: Pd-Catalyzed\nSuzuki–Miyaura Coupling of Nonactivated Propargylamines with\nBoronic Acids

Palladium-catalyzed Suzuki–Miyaura\ncross-coupling is an\nefficient approach for C–C bond construction. Here we report\na deaminative Suzuki–Miyaura reaction to achieve chemo- and\nregioselectivity in the cross-coupling of nonactivated propargylamines\nwith boronic acids, in which methyl propiolate is introduced to promote\nthe cleavage of the C–N bond to form the C–C bond. This\nmethod features a wide range of substrates, good functional group\ntolerance, and ease of operation, providing an alternative approach\nto accessing valuable propargylated aromatic compounds.

Publication Details

Journal
Figshare
Published
2024-08-31
DOI
https://doi.org/10.1021/acs.joc.4c01519.s001
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Precision Propargylic\nSubstitution Reaction: Pd-Catalyzed\nSuzuki–Miyaura Coupling of Nonactivated Propargylamines with\nBoronic Acids

Figshare
Catalytic Cross-Coupling Reactions
article

Precision Propargylic\nSubstitution Reaction: Pd-Catalyzed\nSuzuki–Miyaura Coupling of Nonactivated Propargylamines with\nBoronic Acids

article en

Abstract

Palladium-catalyzed Suzuki–Miyaura\ncross-coupling is an\nefficient approach for C–C bond construction. Here we report\na deaminative Suzuki–Miyaura reaction to achieve chemo- and\nregioselectivity in the cross-coupling of nonactivated propargylamines\nwith boronic acids, in which methyl propiolate is introduced to promote\nthe cleavage of the C–N bond to form the C–C bond. This\nmethod features a wide range of substrates, good functional group\ntolerance, and ease of operation, providing an alternative approach\nto accessing valuable propargylated aromatic compounds.

Figshare
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Catalytic Cross-Coupling Reactions
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Precision Propargylic\nSubstitution Reaction: Pd-Catalyzed\nSuzuki–Miyaura Coupling of Nonactivated Propargylamines with\nBoronic Acids · Figshare (2024) | TGRS Research Map | TGRS