氧化石墨烯催化吲哚与环氧化物的区域和对映选择性傅克反应：一种绿色方法。

Regio- and enantioselective friedel-crafts reactions of indoles to epoxides catalyzed by graphene oxide: a green approach.

作者信息

Acocella Maria Rosaria, Mauro Marco, Guerra Gaetano

机构信息

Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, 84080 Fisciano (Sa) (Italy).

出版信息

ChemSusChem. 2014 Dec;7(12):3279-83. doi: 10.1002/cssc.201402770. Epub 2014 Oct 19.

DOI:10.1002/cssc.201402770

PMID:25328083

Abstract

Graphene oxide efficiently promotes high regio- and enantioselective ring opening reactions of aromatic epoxides by indoles addition, in solvent- and metal-free conditions. The Friedel-Crafts products were obtained with enantioselectivity up to 99 % ee. The complete inversion of stereochemistry indicates the occurrence of SN 2-type reaction, which assures high level of enantioselectivity.

摘要

氧化石墨烯在无溶剂和无金属条件下，通过吲哚加成高效地促进了芳香族环氧化物的高区域和对映选择性开环反应。得到了对映选择性高达99% ee的傅克产物。立体化学的完全翻转表明发生了SN2型反应，这确保了高水平的对映选择性。