Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System

Joon Young Hwang; Jong Hwa Baek; Tae Il Shin; Jung Ha Shin; Jae Won Oh; Kwang Pyo Kim; Youngmin You; Eun Joo Kang

doi:10.1021/acs.orglett.6b02375

Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)₅ and Phenanthroline System

Joon Young Hwang, Jong Hwa Baek, Tae Il Shin, Jung Ha Shin, Jae Won Oh, Kwang Pyo Kim, Youngmin You, Eun Joo Kang

Department of Chemical Engineering & Materials Science

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

25 Scopus citations

Abstract

An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)₅] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)₅, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.

Original language	English
Pages (from-to)	4900-4903
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6b02375
State	Published - 7 Oct 2016

Bibliographical note

Funding Information:
This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (Grant Nos. NRF-2012R1A1A1044770 and NRF-2015R1D1A1A01060349)

Publisher Copyright:
© 2016 American Chemical Society.

Access to Document

10.1021/acs.orglett.6b02375

Cite this

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title = "Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System",

abstract = "An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.",

author = "Hwang, {Joon Young} and Baek, {Jong Hwa} and Shin, {Tae Il} and Shin, {Jung Ha} and Oh, {Jae Won} and Kim, {Kwang Pyo} and Youngmin You and Kang, {Eun Joo}",

note = "Funding Information: This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (Grant Nos. NRF-2012R1A1A1044770 and NRF-2015R1D1A1A01060349) Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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language = "English",

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T2 - Fe(CO)5 and Phenanthroline System

AU - Hwang, Joon Young

AU - Baek, Jong Hwa

AU - Shin, Tae Il

AU - Shin, Jung Ha

AU - Oh, Jae Won

AU - Kim, Kwang Pyo

AU - You, Youngmin

AU - Kang, Eun Joo

N1 - Funding Information: This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (Grant Nos. NRF-2012R1A1A1044770 and NRF-2015R1D1A1A01060349) Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/10/7

Y1 - 2016/10/7

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AB - An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.

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