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

9 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

Access to Document

10.1021/acs.orglett.4c00755

Cite this

@article{132b30b1776e405392a005943e016e0b,

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.",

year = "2024",

month = apr,

day = "19",

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

language = "English",

volume = "26",

pages = "3145--3150",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=85189524677&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.4c00755

DO - 10.1021/acs.orglett.4c00755

M3 - Article

C2 - 38551489

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this