Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen.

J Org Chem

Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, Pesaro and Urbino (PU), Italy.

Published: August 2017

We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and HO that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis of the preliminary experimental observations, we propose that the reaction proceeds through a borrowing hydrogen process.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.7b01603DOI Listing

Publication Analysis

Top Keywords

benzyl alcohols
8
borrowing hydrogen
8
iron-catalyzed direct
4
direct c3-benzylation
4
c3-benzylation indoles
4
indoles benzyl
4
alcohols borrowing
4
hydrogen coupling
4
coupling primary
4
primary secondary
4

Similar Publications

The development of sustainable synthetic methods for converting alcohols to amines is of great interest due to their widespread use in pharmaceuticals and fine chemicals. In this work, we present an electrochemical approach by using green electrons for the selective oxidation of benzyl alcohol to benzaldehyde using a NiOOH catalyst, followed by its reductive amination to form benzyl--butylamine. The number of Ni monolayer equivalents on the catalyst was found to significantly influence selectivity, with 2 monolayers achieving up to 90% faradaic efficiency (FE) for benzaldehyde in NaOH, while 10 monolayers performed best in a -butylamine solution (pH 11), yielding 100% FE for benzaldehyde.

View Article and Find Full Text PDF

Objective: To compare the effectiveness and safety of budesonide-glycopyrrolate-formoterol, a twice daily metered dose inhaler, and fluticasone-umeclidinium-vilanterol, a once daily dry powder inhaler, in patients with chronic obstructive pulmonary disease (COPD) treated in routine clinical practice.

Design: New user cohort study.

Setting: Longitudinal commercial US claims data.

View Article and Find Full Text PDF

Stroke is the leading cause of death and disability worldwide, with ischemic stroke accounting for the majority of these. HBA is the active ingredient in and has potential therapeutic effects on central nervous system diseases. In this study, the cell model of cerebral ischemia was replicated by the culture method of oxygen-glucose deprivation/reoxygenation, and the rat model of vascular dementia was established by the two-vessel occlusion method.

View Article and Find Full Text PDF

Ni(II)-hydrazineylpyridine (Ni(II)-PyH)-catalyzed regioselective synthesis of α-benzyl substituted β-hydroxy ketones from α,β-unsaturated ketones and alcohols is reported a Fenton free-radical reaction. This protocol enables facile access to desired products in good to excellent yields in 12 h using toluene solvent at room temperature to 100 °C. The structural analysis of the products was confirmed by H, C-NMR, GC-MS, and HRMS data.

View Article and Find Full Text PDF

The second 3d-transition metal incorporation in Ni-(oxy)hydroxide has a drastic effect on alkaline OER and alcohol dehydrogenation reactivity. While Mn incorporation suppresses the alkaline OER, it greatly improves the alcohol dehydrogenation reactivity. A complete reversal of reactivity is obtained when Fe is incorporated, which shows better performance for alkaline OER with poor alcohol dehydrogenation reactivity.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!