Iron-catalyzed peroxidation–carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp2)–H functionalization

Jun-Kee Cheng; Liang Shen; Liu-Hai Wu; Xu-Hong Hu; Teck-Peng Loh

doi:10.1039/C7CC08074C

Iron-catalyzed peroxidation–carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp²)–H functionalization

Jun-Kee Cheng,^b Liang Shen,^b Liu-Hai Wu,^b Xu-Hong Hu*^a and Teck-Peng Loh*^a^b

Author affiliations

* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China
E-mail: ias_xhhu@njtech.edu.cn

^b Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
E-mail: teckpeng@ntu.edu.sg

Abstract

A reaction protocol in which FeCl₃ and tert-butyl hydroperoxide facilitated a selective radical coupling reaction of aryl alkenes or 1,3-enynes with tert-butyl hydroperoxide and formamides to prepare an array of β-peroxy amides has been achieved. The β-peroxy amide could serve as a synthetic precursor which was facilely converted to β-hydroxy amide, β-keto amide and β-lactam following subsequent chemical transformation.

Supplementary files

Publication details

The article was received on 19 Oct 2017, accepted on 01 Nov 2017 and first published on 01 Nov 2017

Article type: Communication

DOI: 10.1039/C7CC08074C

Citation: Chem. Commun., 2017,53, 12830-12833

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Iron-catalyzed peroxidation–carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp²)–H functionalization

J. Cheng, L. Shen, L. Wu, X. Hu and T. Loh, Chem. Commun., 2017, 53, 12830
DOI: 10.1039/C7CC08074C
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Chemical Communications

Iron-catalyzed peroxidation–carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp²)–H functionalization

Abstract

Supplementary files

Publication details

Iron-catalyzed peroxidation–carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp²)–H functionalization

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