Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

Zhen Lin Hou; Fan Yang; Zhibing Zhou; Yu Fei Ao; Bo Yao

doi:10.1016/j.tetlet.2018.11.026

Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

Zhen Lin Hou, Fan Yang, Zhibing Zhou, Yu Fei Ao, Bo Yao^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

4 Citations (Scopus)

Abstract

A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

Original language	English
Pages (from-to)	4557-4561
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.026
Publication status	Published - 26 Dec 2018

Keywords

Allyl(trimethyl)silane
Cross-coupling
Palladium catalysis
Silver salt

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10.1016/j.tetlet.2018.11.026

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title = "Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis",

abstract = "A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.",

keywords = "Allyl(trimethyl)silane, Cross-coupling, Palladium catalysis, Silver salt",

author = "Hou, {Zhen Lin} and Fan Yang and Zhibing Zhou and Ao, {Yu Fei} and Bo Yao",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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day = "26",

doi = "10.1016/j.tetlet.2018.11.026",

language = "English",

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T1 - Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

AU - Hou, Zhen Lin

AU - Yang, Fan

AU - Zhou, Zhibing

AU - Ao, Yu Fei

AU - Yao, Bo

PY - 2018/12/26

Y1 - 2018/12/26

N2 - A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

AB - A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

KW - Allyl(trimethyl)silane

KW - Cross-coupling

KW - Palladium catalysis

KW - Silver salt

UR - http://www.scopus.com/inward/record.url?scp=85056854203&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.11.026

DO - 10.1016/j.tetlet.2018.11.026

M3 - Article

AN - SCOPUS:85056854203

SN - 0040-4039

VL - 59

SP - 4557

EP - 4561

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

Abstract

Keywords

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