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Literature DB >> 21902212

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

Aditya Kulkarni¹, 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.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2011 PMID： 21902212 PMCID： PMC3184324 DOI： 10.1021/ol2019899

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

12 in total

1. CC-1065 and the Duocarmycins: Synthetic Studies.

Authors: Dale L. Boger; Christopher W. Boyce; Robert M. Garbaccio; Joel A. Goldberg
Journal: Chem Rev Date: 1997-05-08 Impact factor: 60.622

2. Asymmetric hydrogenation of heteroaromatic compounds.

Authors: Yong-Gui Zhou
Journal: Acc Chem Res Date: 2007-09-27 Impact factor: 22.384

3. Iridium-catalyzed asymmetric hydrogenation of N-protected indoles.

Authors: Alejandro Baeza; Andreas Pfaltz
Journal: Chemistry Date: 2010-02-15 Impact factor: 5.236

Review 4. The reduction of indoles and related compounds.

Authors: B Robinson
Journal: Chem Rev Date: 1969-12 Impact factor: 60.622

5. Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids.

Authors: Duo-Sheng Wang; Qing-An Chen; Wei Li; Chang-Bin Yu; Yong-Gui Zhou; Xumu Zhang
Journal: J Am Chem Soc Date: 2010-07-07 Impact factor: 15.419

6. Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles.

Authors: Ryoichi Kuwano; Kohei Kaneda; Takashi Ito; Koji Sato; Takashi Kurokawa; Yoshihiko Ito
Journal: Org Lett Date: 2004-06-24 Impact factor: 6.005

7. Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme.

Authors: Ramanathan Natesh; Sylva L U Schwager; Hazel R Evans; Edward D Sturrock; K Ravi Acharya
Journal: Biochemistry Date: 2004-07-13 Impact factor: 3.162

8. Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis.

Authors: Rajesh Viswanathan; Erode N Prabhakaran; Michael A Plotkin; Jeffrey N Johnston
Journal: J Am Chem Soc Date: 2003-01-08 Impact factor: 15.419

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

1. CC-1065 and the Duocarmycins: Synthetic Studies.

2. Asymmetric hydrogenation of heteroaromatic compounds.

3. Iridium-catalyzed asymmetric hydrogenation of N-protected indoles.

Review 4. The reduction of indoles and related compounds.

5. Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids.

6. Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles.

7. Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme.

8. Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis.

9. Angiotensin converting enzyme inhibitors: 1-glutarylindoline-2-carboxylic acids derivatives.

10. Brønsted acid mediated tandem Diels-Alder/aromatization reactions of vinylindoles.

1. Dirhodium-catalyzed C-H arene amination using hydroxylamines.

2. Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals.

3. Study of catalytic hydrogenation and dehydrogenation of 2,3-dimethylindole for hydrogen storage application.