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Few Layer 2D Pnictogens (P & Sb) Catalyze the Alkylation of Soft Nucleophiles with Esters

preprint
submitted on 25.09.2018 and posted on 26.09.2018 by 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

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. Thus, the Calkyl–O bond of the ester is selectively activated on the catalytic pnictogen surface with respect to the much more reactive neighboring C–C and C=O bonds, allowing the alkylation of a variety of acid–sensitive organic molecules and giving synthetic relevancy to the use of simple esters as alkylating agents.

History

Email Address of Submitting Author

gonzalo.abellan@fau.de

Institution

Friedrich– Alexander–Universität Erlangen–Nürnberg (FAU)

Country

Germany

ORCID For Submitting Author

0000-0003-1564-6210

Declaration of Conflict of Interest

The authors declare no conflict of interest

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