Literature DB >> 16771464

Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals.

Seiji Suga1, Kouichi Matsumoto, Koji Ueoka, Jun-ichi Yoshida.   

Abstract

A sequential one-pot indirect cation pool method has been developed. The method involves the electrochemical generation and accumulation of ArS(ArSSAr)+ at low temperature (step 1) and the follow-up reaction with a thioacetal to generate an alkoxycarbenium ion pool (step 2), which reacts with various carbon nucleophiles (step 3). Steps 2 and 3 are extremely fast. The electrogenerated ArS(ArSSAr)+ was well-characterized by 1H NMR and CSI-MS. The alkoxycarbenium ion pool generated by the present indirect method exhibited 1H and 13C NMR spectra and thermal stability similar to those of the alkoxycarbenium ion pool generated by the direct electrochemical method.

Entities:  

Year:  2006        PMID： 16771464     DOI： 10.1021/ja0625778

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

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Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

2.  Electrochemical generation of glycosyl triflate pools.

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Journal:  J Am Chem Soc       Date:  2007-08-14       Impact factor: 15.419

3.  Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes.

Authors:  Philipp Röse; Steffen Emge; Jun-Ichi Yoshida; Gerhard Hilt
Journal:  Beilstein J Org Chem       Date:  2015-01-28       Impact factor: 2.883

4.  Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides.

Authors:  Akihiro Shimizu; Ryutaro Hayashi; Yosuke Ashikari; Toshiki Nokami; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2015-02-13       Impact factor: 2.883

Review 5.  Recent advances in the electrochemical construction of heterocycles.

Authors:  Robert Francke
Journal:  Beilstein J Org Chem       Date:  2014-12-03       Impact factor: 2.883

6.  Redox active dendronized polystyrenes equipped with peripheral triarylamines.

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Journal:  Beilstein J Org Chem       Date:  2014-12-22       Impact factor: 2.883

7.  Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations.

Authors:  Koichi Mitsudo; Junya Yamamoto; Tomoya Akagi; Atsuhiro Yamashita; Masahiro Haisa; Kazuki Yoshioka; Hiroki Mandai; Koji Ueoka; Christian Hempel; Jun-Ichi Yoshida; Seiji Suga
Journal:  Beilstein J Org Chem       Date:  2018-05-24       Impact factor: 2.883

Review 8.  Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products.

Authors:  Sabine Möhle; Michael Zirbes; Eduardo Rodrigo; Tile Gieshoff; Anton Wiebe; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-19       Impact factor: 15.336
  8 in total

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