Literature DB >> 25820636

Phase-transfer and other types of catalysis with cyclopropenium ions.

Jeffrey S Bandar1, Anont Tanaset, Tristan H Lambert.   

Abstract

This work establishes the cyclopropenium ion as a viable platform for efficient phase-transfer catalysis of a diverse range of organic transformations. The amenability of these catalysts to large-scale synthesis and structural modification is demonstrated. Evaluation of the molecular structure of an optimal catalyst reveals some unique structural features of these systems. Finally, a discussion of electronic charge distribution underscores an important consideration for catalyst design.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aromatic ions; aromaticity; cyclopropenium; phase-transfer catalysis; structure-activity relationships

Mesh:

Substances:

Year:  2015        PMID: 25820636      PMCID: PMC4617660          DOI: 10.1002/chem.201500124

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  20 in total

1.  A stable chiral diaminocyclopropenylidene.

Authors:  Dirk Holschumacher; Cristian G Hrib; Peter G Jones; Matthias Tamm
Journal:  Chem Commun (Camb)       Date:  2007-06-25       Impact factor: 6.222

Review 2.  Recent development and application of chiral phase-transfer catalysts.

Authors:  Takuya Hashimoto; Keiji Maruoka
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

3.  A class of phase-transfer catalyst with interionic strain: insight into the bonding of disubstituted N- vs carbene-stabilized N(I)-centered cations.

Authors:  Roya Mirabdolbaghi; Travis Dudding; Theocharis Stamatatos
Journal:  Org Lett       Date:  2014-05-23       Impact factor: 6.005

4.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

5.  Synthesis, structure, and reactivity of carbene-stabilized phosphorus(III)-centered trications [L3P]3+.

Authors:  Jekaterina Petuškova; Mahendra Patil; Sigrid Holle; Christian W Lehmann; Walter Thiel; Manuel Alcarazo
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

6.  Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions.

Authors:  Ting Ma; Xiao Fu; Choon Wee Kee; Lili Zong; Yuanhang Pan; Kuo-Wei Huang; Choon-Hong Tan
Journal:  J Am Chem Soc       Date:  2011-02-11       Impact factor: 15.419

7.  Triaminocyclopropenium salts as ionic liquids.

Authors:  Owen J Curnow; Douglas R MacFarlane; Kelvin J Walst
Journal:  Chem Commun (Camb)       Date:  2011-08-17       Impact factor: 6.222

8.  Exploiting the π-acceptor properties of carbene-stabilized phosphorus centered trications [L3P]3+: applications in Pt(II) catalysis.

Authors:  Javier Carreras; Mahendra Patil; Walter Thiel; Manuel Alcarazo
Journal:  J Am Chem Soc       Date:  2012-09-25       Impact factor: 15.419

9.  Stable Bis(diisopropylamino)cyclopropenylidene (BAC) as Ligand for Transition Metal Complexes.

Authors:  Glenn Kuchenbeiser; Bruno Donnadieu; Guy Bertrand
Journal:  J Organomet Chem       Date:  2008-03-01       Impact factor: 2.369

10.  The synthesis of organic carbonates from carbon dioxide.

Authors:  Toshiyasu Sakakura; Kazufumi Kohno
Journal:  Chem Commun (Camb)       Date:  2009-01-28       Impact factor: 6.222

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  4 in total

1.  Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.

Authors:  Tyler K Heiss; Jennifer A Prescher
Journal:  J Org Chem       Date:  2019-05-28       Impact factor: 4.354

2.  Highly-fluorinated Triaminocyclopropenium Ionic Liquids.

Authors:  Owen J Curnow; Rathiga Senthooran
Journal:  Chem Asian J       Date:  2022-03-16

3.  Catalytic Synthesis of Cyclopropenium Cations with Rh-Carbynoids.

Authors:  Hang-Fei Tu; Aliénor Jeandin; Marcos G Suero
Journal:  J Am Chem Soc       Date:  2022-09-08       Impact factor: 16.383

4.  Self-Assembly of Aminocyclopropenium Salts: En Route to Deltic Ionic Liquid Crystals.

Authors:  Juri Litterscheidt; Jeffrey S Bandar; Max Ebert; Robert Forschner; Korinna Bader; Tristan H Lambert; Wolfgang Frey; Andrea Bühlmeyer; Marcus Brändle; Finn Schulz; Sabine Laschat
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-07       Impact factor: 15.336

  4 in total

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