Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

Kazuhiro Okamoto; Naoki Shida; Mahito Atobe

doi:10.3762/bjoc.20.27

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

Translated title of the contribution: Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

Kazuhiro Okamoto, Naoki Shida, Mahito Atobe

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

2 Scopus citations

Abstract

Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.

Translated title of the contribution	Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process
Original language	English
Pages (from-to)	264-271
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	20
DOIs	https://doi.org/10.3762/bjoc.20.27
State	Published - 2024/02/12
Externally published	Yes

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title = "Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process",

abstract = "Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.",

author = "Kazuhiro Okamoto and Naoki Shida and Mahito Atobe",

year = "2024",

month = feb,

day = "12",

doi = "10.3762/bjoc.20.27",

language = "英語",

volume = "20",

pages = "264--271",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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T1 - Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

AU - Okamoto, Kazuhiro

AU - Shida, Naoki

AU - Atobe, Mahito

PY - 2024/2/12

Y1 - 2024/2/12

N2 - Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.

AB - Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.

U2 - 10.3762/bjoc.20.27

DO - 10.3762/bjoc.20.27

M3 - 学術論文

C2 - 38379733

SN - 1860-5397

VL - 20

SP - 264

EP - 271

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

Abstract

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