Next Article in Journal
Photocatalytic Degradation of Acridine Orange over NaBiO3 Driven by Visible Light Irradiation
Next Article in Special Issue
Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant
Previous Article in Journal
Specific Facets-Dominated Anatase TiO2: Fluorine-Mediated Synthesis and Photoactivity
Open AccessArticle

Mechanistic Studies for Synthesis of Bis(indolyl)methanes: Pd-Catalyzed C–H Activation of Indole–Carboxylic Acids with Benzyl Alcohols in Water

Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
*
Authors to whom correspondence should be addressed.
Catalysts 2013, 3(2), 486-500; https://doi.org/10.3390/catal3020486
Received: 27 March 2013 / Revised: 9 May 2013 / Accepted: 10 May 2013 / Published: 16 May 2013
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
A method for synthesis without protecting groups of bis(indolyl)methanes by the (η3-benzyl)palladium system generated from a palladium catalyst and benzyl alcohol in water is developed. This domino protocol involves C3–H bond activation/benzylation of indole–carboxylic acids and benzylic C–H functionalization. Mechanistic studies indicate that the (η3-benzyl)palladium(II) complex, which is formed via oxidative addition of benzyl alcohol 2 to a Pd(0) species, activates the C–H bond at the C3-position of indole 1. Notably, water plays an important role in our catalytic system for sp3 C–O bond activation and stabilization of OH by hydration for the smooth generation of the activated Pd(II) cation species, as well as for nucleophilic attack of indoles to hydrated benzyl alcohols. View Full-Text
Keywords: palladium; C–H activation; water; indole; benzyl alcohol palladium; C–H activation; water; indole; benzyl alcohol
Show Figures

Figure 1

MDPI and ACS Style

Hikawa, H.; Suzuki, H.; Yokoyama, Y.; Azumaya, I. Mechanistic Studies for Synthesis of Bis(indolyl)methanes: Pd-Catalyzed C–H Activation of Indole–Carboxylic Acids with Benzyl Alcohols in Water. Catalysts 2013, 3, 486-500.

Show more citation formats Show less citations formats

Article Access Map

1
Only visits after 24 November 2015 are recorded.
Back to TopTop