Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Ryutaro Hayashi; Akihiro Shimizu; Jonathan Davies; Yu Ishizaki; Chris Willis; Jun-ichi Yoshida

doi:10.1002/anie.201807592

Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Ryutaro Hayashi, Akihiro Shimizu, Jonathan Davies, Yu Ishizaki, Chris Willis, Jun-ichi Yoshida

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C−H/aromatic C−H cross-coupling.

Original language	English
Pages (from-to)	12891-12895
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	39
Early online date	29 Aug 2018
DOIs	https://doi.org/10.1002/anie.201807592
Publication status	Published - 24 Sep 2018

Structured keywords

BCS and TECS CDTs

Keywords

benzyl cations
oxidation
C−H functionalization C−H/C−H cross-coupling
electrochemistry
C-H/C-H cross coupling

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10.1002/anie.201807592

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title = "Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions",

abstract = "A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C−H/aromatic C−H cross-coupling.",

keywords = "benzyl cations, oxidation, C−H functionalization C−H/C−H cross-coupling, electrochemistry, C-H/C-H cross coupling",

author = "Ryutaro Hayashi and Akihiro Shimizu and Jonathan Davies and Yu Ishizaki and Chris Willis and Jun-ichi Yoshida",

year = "2018",

month = sep,

day = "24",

doi = "10.1002/anie.201807592",

language = "English",

volume = "57",

pages = "12891--12895",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

AU - Hayashi, Ryutaro

AU - Shimizu, Akihiro

AU - Davies, Jonathan

AU - Ishizaki, Yu

AU - Willis, Chris

AU - Yoshida, Jun-ichi

PY - 2018/9/24

Y1 - 2018/9/24

N2 - A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C−H/aromatic C−H cross-coupling.

AB - A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C−H/aromatic C−H cross-coupling.

KW - benzyl cations

KW - oxidation

KW - C−H functionalization C−H/C−H cross-coupling

KW - electrochemistry

KW - C-H/C-H cross coupling

UR - http://www.scopus.com/inward/record.url?scp=85053032498&partnerID=8YFLogxK

U2 - 10.1002/anie.201807592

DO - 10.1002/anie.201807592

M3 - Article (Academic Journal)

C2 - 30156746

AN - SCOPUS:85053032498

VL - 57

SP - 12891

EP - 12895

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 39

ER -

Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Abstract

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Keywords

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