Literature DB >> 28103032

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

Yu Kitazawa1, Ryo Takita2, Kengo Yoshida2, Atsuya Muranaka2, Seijiro Matsubara3, Masanobu Uchiyama1,2.   

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.

Entities:  

Year:  2017        PMID： 28103032     DOI： 10.1021/acs.joc.6b02677

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C-H Insertion Reactions.

Authors:  Benjamin Wigman; Stasik Popov; Alex L Bagdasarian; Brian Shao; Tyler R Benton; Chloé G Williams; Steven P Fisher; Vincent Lavallo; K N Houk; Hosea M Nelson
Journal:  J Am Chem Soc       Date:  2019-05-29       Impact factor: 15.419

2.  Enantiospecific Synthesis of ortho-Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence.

Authors:  Stefan Aichhorn; Raphael Bigler; Eddie L Myers; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-07-06       Impact factor: 15.419

3.  Computational assessments of diastereoselective [4+2] cycloaddition and 1,3-borotopic shift of a dearomatized tertiary boronic ester intermediate: reactivities explained through transition-state distortion energies.

Authors:  Aqeel A Hussein; Faisal A Almalki; Alaa M Alqahtani; Sergey Shityakov
Journal:  RSC Adv       Date:  2019-07-26       Impact factor: 4.036

4.  Highly selective palladium-catalyzed one-pot, five-fold B-H/C-H cross coupling of monocarboranes with alkenes.

Authors:  Yunjun Shen; Kang Zhang; Xuewei Liang; Rakesh Dontha; Simon Duttwyler
Journal:  Chem Sci       Date:  2019-03-04       Impact factor: 9.825
  4 in total

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