Gold-Catalyzed C(sp3)-C(sp2) Suzuki-Miyaura Coupling Reaction

Wenqian Du; Fen Zhao; Rongjie Yang; Zhonghua Xia

doi:10.1021/acs.orglett.4c00755

Gold-Catalyzed C(sp³)-C(sp²) Suzuki-Miyaura Coupling Reaction

Wenqian Du, Fen Zhao, Rongjie Yang, Zhonghua Xia^*

^*Corresponding author for this work

School of Material Science and Engineering

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

A gold-catalyzed C(sp³)-C(sp²) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp³)-C(sp²) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.

Original language	English
Pages (from-to)	3145-3150
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.4c00755
Publication status	Published - 19 Apr 2024

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title = "Gold-Catalyzed C(sp3)-C(sp2) Suzuki-Miyaura Coupling Reaction",

abstract = "A gold-catalyzed C(sp3)-C(sp2) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp3)-C(sp2) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.",

author = "Wenqian Du and Fen Zhao and Rongjie Yang and Zhonghua Xia",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

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doi = "10.1021/acs.orglett.4c00755",

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T1 - Gold-Catalyzed C(sp3)-C(sp2) Suzuki-Miyaura Coupling Reaction

AU - Du, Wenqian

AU - Zhao, Fen

AU - Yang, Rongjie

AU - Xia, Zhonghua

PY - 2024/4/19

Y1 - 2024/4/19

N2 - A gold-catalyzed C(sp3)-C(sp2) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp3)-C(sp2) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.

AB - A gold-catalyzed C(sp3)-C(sp2) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp3)-C(sp2) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.

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U2 - 10.1021/acs.orglett.4c00755

DO - 10.1021/acs.orglett.4c00755

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AN - SCOPUS:85189524677

SN - 1523-7060

VL - 26

SP - 3145

EP - 3150

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Gold-Catalyzed C(sp³)-C(sp²) Suzuki-Miyaura Coupling Reaction

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