Literature DB >> 22813437

Reductive eliminations from λ3-iodanes: understanding selectivity and the crucial role of the hypervalent bond.

Halua Pinto de Magalhães1, Hans Peter Lüthi, Antonio Togni.   

Abstract

This computational study investigates the factors governing the selectivity of the reductive eliminations from rapidly equilibrating isomeric λ(3)-iodanes derived from a diaryl iodonium salt and a nucleophile. The chemoselectivity is mainly determined by the partial charge at the ipso-carbon atom involved in the 3-center-4-electron bond.

Entities:  

Year:  2012        PMID： 22813437     DOI： 10.1021/ol3014039

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Crystal Structures of Diaryliodonium Fluorides and Their Implications for Fluorination Mechanisms.

Authors:  Yong-Sok Lee; Joong-Hyun Chun; Milan Hodošček; Victor W Pike
Journal:  Chemistry       Date:  2017-03-02       Impact factor: 5.236

2.  Iodonium metathesis reactions.

Authors:  Takahito Kasahara; Young Jin Jang; Léanne Racicot; Dimitrios Panagopoulos; Steven H Liang; Marco A Ciufolini
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

3.  Orbital analysis of bonding in diarylhalonium salts and relevance to periodic trends in structure and reactivity.

Authors:  Shubhendu S Karandikar; Avik Bhattacharjee; Bryan E Metze; Nicole Javaly; Edward J Valente; Theresa M McCormick; David R Stuart
Journal:  Chem Sci       Date:  2022-05-19       Impact factor: 9.969

4.  Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in Copper Catalysis.

Authors:  Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal:  Organometallics       Date:  2014-09-22       Impact factor: 3.876

5.  Fast and highly chemoselective alkynylation of thiols with hypervalent iodine reagents enabled through a low energy barrier concerted mechanism.

Authors:  Reto Frei; Matthew D Wodrich; Durga Prasad Hari; Pierre-Antoine Borin; Clément Chauvier; Jérôme Waser
Journal:  J Am Chem Soc       Date:  2014-11-13       Impact factor: 15.419

6.  Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.

Authors:  Elin Stridfeldt; Erik Lindstedt; Marcus Reitti; Jan Blid; Per-Ola Norrby; Berit Olofsson
Journal:  Chemistry       Date:  2017-09-05       Impact factor: 5.236

7.  Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts.

Authors:  Gabriella Kervefors; Leonard Kersting; Berit Olofsson
Journal:  Chemistry       Date:  2021-03-03       Impact factor: 5.236

8.  Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study.

Authors:  Joel Malmgren; Stefano Santoro; Nazli Jalalian; Fahmi Himo; Berit Olofsson
Journal:  Chemistry       Date:  2013-06-20       Impact factor: 5.236

9.  Mechanistic Studies and Radiofluorination of Structurally Diverse Pharmaceuticals with Spirocyclic Iodonium(III) Ylides.

Authors:  Benjamin H Rotstein; Lu Wang; Richard Y Liu; Jon Patteson; Eugene E Kwan; Neil Vasdev; Steven H Liang
Journal:  Chem Sci       Date:  2016-03-24       Impact factor: 9.825

10.  Metal-free formal synthesis of phenoxazine.

Authors:  Gabriella Kervefors; Antonia Becker; Chandan Dey; Berit Olofsson
Journal:  Beilstein J Org Chem       Date:  2018-06-20       Impact factor: 2.883
  10 in total

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