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“裸露”的锂离子:受硼烷阴离子作用而被强烈激活的金属阳离子。

"Naked" Lithium Cation: Strongly Activated Metal Cations Facilitated by Carborane Anions.

机构信息

Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Elements Chemistry Laboratory, RIKEN, and Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science (CSRS) , 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.

出版信息

J Org Chem. 2017 Feb 17;82(4):1931-1935. doi: 10.1021/acs.joc.6b02677. Epub 2017 Jan 27.

Abstract

Experimental and spectroscopic studies revealed unprecedented reactivity of a "naked" lithium cation with very weakly coordinating anions, including carborane anions. The superactivated lithium cation has greatly enhanced Lewis acidic character and mediates various organic reactions such as carbonyl-ene reaction, NBS-bromination of unactivated aromatics, and Friedel-Crafts alkylation, which are not promoted by conventional lithium salts. Chemical robustness of the counteranion also plays an important role in the chemistry of the strongly activated lithium cation.

摘要

实验和光谱研究揭示了“裸露”的锂离子与非常弱配位阴离子(包括硼烷阴离子)前所未有的反应性。超活化的锂离子具有大大增强的路易斯酸性,并介导各种有机反应,如羰基-烯反应、未活化芳环的 NBS 溴化和傅-克烷基化,这些反应不受常规锂盐的促进。抗衡阴离子的化学稳定性在强活化锂离子的化学中也起着重要作用。

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