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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3054
Title: Chemoselective N-Alkylation of Indoles in Aqueous Microdroplets
Authors: Gnanamani, Elumalai
Yan X.
Zare R.N.
Published in: Angewandte Chemie - International Edition
Abstract: Many reactions show much faster kinetics in microdroplets than in the bulk phase. Most reported reactions in microdroplets mirror the products found in bulk reactions. However, the unique environment of microdroplets allows different chemistry to occur. In this work, we present the first chemoselective N-alkylation of indoles in aqueous microdroplets via a three-component Mannich-type reaction without using any catalyst. In sharp contrast, bulk reactions using the same reagents with a catalyst yield exclusively C-alkylation products. The N-alkylation yield is moderate in microdroplets, up to 53 %. We extended the scope of the microdroplet reaction and obtained a series of new functionalized indole aminals, which are likely to have biological activities. This work clearly indicates that microdroplet reactions can show reactivity quite different from that of bulk-phase reactions, which holds great potential for developing novel reactivities in microdroplets. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Citation: Angewandte Chemie - International Edition (2020), 59(8): 3069-3072
URI: https://doi.org/10.1002/anie.201913069
http://repository.iitr.ac.in/handle/123456789/3054
Issue Date: 2020
Publisher: Wiley-VCH Verlag
Keywords: chemoselectivity
indoles
liquid microdroplets
N-alkylation
reaction acceleration
ISSN: 14337851
Author Scopus IDs: 35319775800
56508695600
35355951800
Author Affiliations: Gnanamani, E., Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305-5080, United States, Department of Chemistry, Fudan University, Shanghai, 200438, China
Yan, X., Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305-5080, United States, Department of Chemistry, Texas A&M University, 580 Ross Street, College Station, TX 77843-3255, United States
Zare, R.N., Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305-5080, United States, Department of Chemistry, Fudan University, Shanghai, 200438, China
Funding Details: We thank Prof. Hao Chen for valuable suggestions and Dr. Vijaya Lakshmi Kanchustambham for help with recording mass spectra. This work was supported by the Scientific Research Startup Foundation (Grant IDH1615113) of Fudan University and the United States Air Force Office of Scientific Research through a Basic Research Initiative grant (AFOSR FA9550-16-1-0113).
Corresponding Author: Zare, R.N.; Department of Chemistry, Stanford University, 333 Campus Drive, United States; email: zare@stanford.edu
Appears in Collections:Journal Publications [CY]

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