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

Research output: Contribution to journalArticlepeer-review

24 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 languageEnglish
Pages (from-to)4900-4903
Number of pages4
JournalOrganic Letters
Volume18
Issue number19
DOIs
StatePublished - 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.

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