Thioamidate Ion as Effective Cocatalyst for Photoinduced CH Alkylation via Multisite Proton-coupled Electron Transfer

Kohsuke Ohmatsu; Haruka Fujimori; Kodai Minami; Kosuke Nomura; Mari Kiyokawa; Takashi Ooi

doi:10.1246/cl.220026

Thioamidate Ion as Effective Cocatalyst for Photoinduced CH Alkylation via Multisite Proton-coupled Electron Transfer

Kohsuke Ohmatsu
, Haruka Fujimori
, Kodai Minami
, Kosuke Nomura
, Mari Kiyokawa
, Takashi Ooi

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

3 Citations (Scopus)

Abstract

Thioamidate ions are introduced as competent cocatalysts for multisite proton-coupled electron transfer (MS-PCET) catalysis. The effectiveness of these anions is ascribed to the high pK_a values of their conjugate acids. The combined use of bench-stable tetrabutylammonium thioamidate with an appropriate Ir-based photosensitizer allows the CH alkylation of a range of CH donors, including simple cyclic alkanes, under visible-light irradiation.

Original language	English
Pages (from-to)	445-447
Number of pages	3
Journal	Chemistry Letters
Volume	51
Issue number	4
DOIs	https://doi.org/10.1246/cl.220026
Publication status	Published - 2022 Apr
Externally published	Yes

Keywords

C–H functionalization
Photoredox catalysis
Proton-coupled electron transfer

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1246/cl.220026

Cite this

@article{5a008d523f7d485081fa3640c0e0dd58,

title = "Thioamidate Ion as Effective Cocatalyst for Photoinduced CH Alkylation via Multisite Proton-coupled Electron Transfer",

abstract = "Thioamidate ions are introduced as competent cocatalysts for multisite proton-coupled electron transfer (MS-PCET) catalysis. The effectiveness of these anions is ascribed to the high pKa values of their conjugate acids. The combined use of bench-stable tetrabutylammonium thioamidate with an appropriate Ir-based photosensitizer allows the CH alkylation of a range of CH donors, including simple cyclic alkanes, under visible-light irradiation.",

keywords = "C{\textendash}H functionalization, Photoredox catalysis, Proton-coupled electron transfer",

author = "Kohsuke Ohmatsu and Haruka Fujimori and Kodai Minami and Kosuke Nomura and Mari Kiyokawa and Takashi Ooi",

note = "Publisher Copyright: {\textcopyright} 2022 The Chemical Society of Japan",

year = "2022",

month = apr,

doi = "10.1246/cl.220026",

language = "English",

volume = "51",

pages = "445--447",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Oxford University Press",

number = "4",

}

TY - JOUR

T1 - Thioamidate Ion as Effective Cocatalyst for Photoinduced CH Alkylation via Multisite Proton-coupled Electron Transfer

AU - Ohmatsu, Kohsuke

AU - Fujimori, Haruka

AU - Minami, Kodai

AU - Nomura, Kosuke

AU - Kiyokawa, Mari

AU - Ooi, Takashi

PY - 2022/4

Y1 - 2022/4

N2 - Thioamidate ions are introduced as competent cocatalysts for multisite proton-coupled electron transfer (MS-PCET) catalysis. The effectiveness of these anions is ascribed to the high pKa values of their conjugate acids. The combined use of bench-stable tetrabutylammonium thioamidate with an appropriate Ir-based photosensitizer allows the CH alkylation of a range of CH donors, including simple cyclic alkanes, under visible-light irradiation.

AB - Thioamidate ions are introduced as competent cocatalysts for multisite proton-coupled electron transfer (MS-PCET) catalysis. The effectiveness of these anions is ascribed to the high pKa values of their conjugate acids. The combined use of bench-stable tetrabutylammonium thioamidate with an appropriate Ir-based photosensitizer allows the CH alkylation of a range of CH donors, including simple cyclic alkanes, under visible-light irradiation.

KW - C–H functionalization

KW - Photoredox catalysis

KW - Proton-coupled electron transfer

UR - https://www.scopus.com/pages/publications/85128208882

UR - https://www.scopus.com/pages/publications/85128208882#tab=citedBy

U2 - 10.1246/cl.220026

DO - 10.1246/cl.220026

M3 - Article

AN - SCOPUS:85128208882

SN - 0366-7022

VL - 51

SP - 445

EP - 447

JO - Chemistry Letters

JF - Chemistry Letters

IS - 4

ER -

Thioamidate Ion as Effective Cocatalyst for Photoinduced CH Alkylation via Multisite Proton-coupled Electron Transfer

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this