Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide

Zeng, Xiaobao; Gu, Qingyun; Dai, Wenjing; Xie, Yushan; Liu, Xin-Yi; Wu, Guixia

doi:10.1055/a-1488-4467

Synthesis

2021

DOI: 10.1055/a-1488-4467

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Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide

Xiaobao Zeng¹,

Qingyun Gu²,

Wenjing Dai³

et al.

Abstract: A rare-earth salts Yb(OTf)3-catalyzed regioselective hydroamination of ynamides with anilines or p-toluenesulfonamide has been developed. This protocol provided facile access to a diverse range of amidines with good group functional group tolerance in moderate to high yield.

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Cited by 3 publications

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Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Mishra,

Sekhar Pati,

Das

2024

Eur J Org Chem

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Most of the methods for the synthesis of functionalized enamides from ynamides were developed in the last two decades showing the contemporary interest in the exploration of ynamide chemistry. The utilization of the intrinsic reactivity of the ynamide triple bond through keteniminium intermediacy, coordination with metals, and as a radical acceptor toward the development of strategies for the synthesis of functionalized enamides reflect the constant strive and creativity in the design and execution of synthetic methods. The present review summarizes the synthetic strategies developed during the last two decades and is divided into the sections depending on the type of hydrofunctionalization reaction. It may be predicted that this field of chemistry will continue to grow exponentially in the coming years and the ready availability of a wide range of ynamides now provides an excellent opportunity to further enrich mainstream synthetic methodologies.

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Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Mishra,

Sekhar Pati,

Das

2024

Eur J Org Chem

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Facile access to α-silylmethylamidines by BF₃-catalyzed hydroamination of silylynamides with amines

Lu,

Li,

Wang

et al. 2024

Org. Biomol. Chem.

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Convenient synthesis of N-sulfonyl α-hydroxyamides via DMSO oxidation of N-alk-1-ynylsulfonamides

Wang

Sheng

et al. 2023

Journal of Sulfur Chemistry

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Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide

Abstract: A rare-earth salts Yb(OTf)3-catalyzed regioselective hydroamination of ynamides with anilines or p-toluenesulfonamide has been developed. This protocol provided facile access to a diverse range of amidines with good group functional group tolerance in moderate to high yield.

Cited by 3 publications

References 2 publications

Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Facile access to α-silylmethylamidines by BF₃-catalyzed hydroamination of silylynamides with amines

Convenient synthesis of N-sulfonyl α-hydroxyamides via DMSO oxidation of N-alk-1-ynylsulfonamides

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Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide

Abstract: A rare-earth salts Yb(OTf)3-catalyzed regioselective hydroamination of ynamides with anilines or p-toluenesulfonamide has been developed. This protocol provided facile access to a diverse range of amidines with good group functional group tolerance in moderate to high yield.

Cited by 3 publications

References 2 publications

Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Facile access to α-silylmethylamidines by BF3-catalyzed hydroamination of silylynamides with amines

Convenient synthesis of N-sulfonyl α-hydroxyamides via DMSO oxidation of N-alk-1-ynylsulfonamides

Contact Info

Product

Resources

About

Facile access to α-silylmethylamidines by BF₃-catalyzed hydroamination of silylynamides with amines