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  • Heterogeneous catalytic hydrogenation of unprotected indoles in water: a green solution to a long-standing challenge.

Heterogeneous catalytic hydrogenation of unprotected indoles in water: a green solution to a long-standing challenge.

Organic letters (2011-09-10)
Aditya Kulkarni, Weihong Zhou, Béla Török
ABSTRACT

An environmentally benign procedure for the hydrogenation of unprotected indoles is described. The hydrogenation reaction is catalyzed by Pt/C and activated by p-toluenesulfonic acid in water as a solvent. The efficacy of the method is illustrated by the hydrogenation of a variety of substituted indoles to their corresponding indolines which were obtained in excellent yields.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Toluenesulfonic acid monohydrate, ACS reagent, ≥98.5%
Sigma-Aldrich
Silver p-toluenesulfonate, ≥99%
Sigma-Aldrich
p-Toluenesulfonic acid monohydrate, ReagentPlus®, ≥98%
Sigma-Aldrich
p-Toluenesulfonic acid monohydrate, SAJ first grade, ≥99.0%
Sigma-Aldrich
Sodium p-toluenesulfonate, 95%