Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters.

Authors: Vicent Lloret1, Miguel Ángel Rivero–Crespo2, José Alejandro Vidal–Moya2, Stefan Wild1, Antonio Doménech–Carbó2, Bettina S. J. Heller3, Sunghwan Shin3, Hans-Peter Steinrück3, Florian Maier3, Frank Hauke1, Maria Varela4, Andreas Hirsch1, Antonio Leyva–Pérez2, Gonzalo Abellán1

  1. Department of Chemistry and Pharmacy and Joint Institute of Advanced Materials and Processes (ZMP) Friedrich–Alexander–Universität Erlangen–Nürnberg (FAU) Henkestrasse 42, 91054 Erlangen and Dr.–Mack Strasse 81, 90762 Fürth, Germany. Phone: +49 91165078–65031; Fax: +49 91165078–65015.
  2. Instituto de Tecnología Química. Universidad Politècnica de València–Consejo Superior de Investigaciones Científicas. Avda. de los Naranjos s/n, 46022, Valencia, Spain. Phone: +34963877800; Fax: +349638 77809.
  3. Chair of Physical Chemistry II, Friedrich–Alexander–Universität Erlangen–Nürnberg (FAU) Egerlandstr. 3, 91058 Erlangen, Germany.
  4. Universidad Complutense de Madrid, Instituto Pluridisciplinar, Instituto de Magnetismo Aplicado & Departamento de Física de Materiales, Madrid 28040, Spain.

DOI10.24435/materialscloud:2018.0021/v1 (version v1, submitted on 11 December 2018)

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How to cite this entry

Vicent Lloret, Miguel Ángel Rivero–Crespo, José Alejandro Vidal–Moya, Stefan Wild, Antonio Doménech–Carbó, Bettina S. J. Heller, Sunghwan Shin, Hans-Peter Steinrück, Florian Maier, Frank Hauke, Maria Varela, Andreas Hirsch, Antonio Leyva–Pérez, Gonzalo Abellán, Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters. , Materials Cloud Archive (2018), doi: 10.24435/materialscloud:2018.0021/v1.

Description

Group 15 elements in zero oxidation state (P, As, Sb and Bi), also called pnictogens, are rarely used in catalysis due to the difficulties associated in preparing well–structured and stable materials. Here, we report on the synthesis of highly exfoliated, few layer 2D phosphorene and antimonene in zero oxidation state, suspended in an ionic liquid, with the native atoms ready to interact with external reagents while avoiding aerobic or aqueous decomposition pathways, and on their use as efficient catalysts for the alkylation of nucleophiles with esters. The few layer pnictogen material circumvents the extremely harsh reaction conditions associated to previous superacid–catalyzed alkylations, by enabling an alternative mechanism on surface, protected from the water and air by the ionic liquid. These 2D catalysts allow the alkylation of a variety of acid–sensitive organic molecules and giving synthetic relevancy to the use of simple esters as alkylating agents.

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Data Availability.
All other data supporting the findings of this study are available within the paper and its supplementary information files.
The source data underlying Figs 1b, 2b–f, Figs 1, 2h,I, and Supplementary Figs S1-S9, Figs S11-S17, Figs S19,20, Figs S22-S24, Figs S28-S30, Figs S32, Figs S34-S40 are provided as a Source Data file
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Keywords

antimonene Black phosphorous alkylation esters ionic liquids

Version history

14 January 2019

11 December 2018 [This version]