Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

He Huang; Zack M. Strater; Tristan H. Lambert

doi:10.1021/jacs.9b11472

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

He Huang, Zack M. Strater, Tristan H. Lambert^*

^*Corresponding author for this work

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

160 Citations (Scopus)

Abstract

The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

Original language	English
Pages (from-to)	1698-1703
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	4
DOIs	https://doi.org/10.1021/jacs.9b11472
Publication status	Published - 29 Jan 2020
Externally published	Yes

Access to Document

10.1021/jacs.9b11472

Cite this

@article{91e2b31f0ca541a7b3ea96588d4c8a9f,

title = "Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity",

abstract = "The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.",

author = "He Huang and Strater, {Zack M.} and Lambert, {Tristan H.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jan,

day = "29",

doi = "10.1021/jacs.9b11472",

language = "English",

volume = "142",

pages = "1698--1703",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

AU - Huang, He

AU - Strater, Zack M.

AU - Lambert, Tristan H.

PY - 2020/1/29

Y1 - 2020/1/29

N2 - The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

AB - The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

UR - http://www.scopus.com/inward/record.url?scp=85078544606&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b11472

DO - 10.1021/jacs.9b11472

M3 - Article

C2 - 31904939

AN - SCOPUS:85078544606

SN - 0002-7863

VL - 142

SP - 1698

EP - 1703

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 4

ER -

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

Abstract

Access to Document

Other files and links

Fingerprint

Cite this