Refining boron-iodane exchange to access versatile arylation reagents

Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components result in improved yield and...

One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

10.26434/chemrxiv.12234665 ◽

2020 ◽

Author(s):

Lucien Caspers ◽

Julian Spils ◽

Mattis Damrath ◽

Enno Lork ◽

Boris Nachtsheim

Keyword(s):

Conformational Analysis ◽

Bronsted Acids ◽

One Pot ◽

Benzyl Alcohols ◽

Iodonium Salts ◽

Efficient Approach ◽

One Pot Synthesis ◽

Diaryliodonium Salts

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

Faculty Opinions recommendation of Cyclic vinyl(aryl)iodonium salts: synthesis and reactivity.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.736500184.793564476 ◽

2019 ◽

Author(s):

Mahesh Lakshman

Keyword(s):

Cooperative Bond Activation and Facile Intramolecular Aryl Transfer of Nickel‐Aluminum Pincer‐type Complexes

Angewandte Chemie International Edition ◽

10.1002/anie.202104050 ◽

2021 ◽

Author(s):

Connie C. Lu ◽

Brendan J. Graziano ◽

Matthew V. Vollmer

Keyword(s):

Bond Activation ◽

Nickel Aluminum ◽

ChemInform Abstract: A Novel Ferrocenyl Diselenide for the Catalytic Asymmetric Aryl Transfer to Aldehydes.

ChemInform ◽

10.1002/chin.200119042 ◽

2001 ◽

Vol 32 (19) ◽

pp. no-no

Author(s):

Carsten Bolm ◽

Martin Kesselgruber ◽

Achim Grenz ◽

Nina Hermanns ◽

Jens P. Hildebrand

Keyword(s):

Catalytic Asymmetric ◽

Fast atom bombardment and secondary ion mass spectra of iodonium salts: Interpretation of spectra and implications for sputtering mechanisms

Organic Mass Spectrometry ◽

10.1002/oms.1210240606 ◽

1989 ◽

Vol 24 (6) ◽

pp. 391-397 ◽

Cited By ~ 7

Author(s):

Kevin L. Duffin ◽

Kenneth L. Busch ◽

Atilla Tuncay

Keyword(s):

Mass Spectra ◽

Fast Atom Bombardment ◽

Iodonium Salts ◽

Secondary Ion

Acetylenic and Ethylenic Iodonium Salts and Their Reactions with a Carbanion1,2

The Journal of Organic Chemistry ◽

10.1021/jo01017a053 ◽

1965 ◽

Vol 30 (6) ◽

pp. 1930-1934 ◽

Cited By ~ 75

Author(s):

F. Marshall Beringer ◽

Suzanne A. Galton

Keyword(s):

ChemInform Abstract: Synthesis of Novel Vinylbenziodoxolones (II) from Alkynyl(o- carboxyphenyl)iodonium Salts (I).

ChemInform ◽

10.1002/chin.199648194 ◽

2010 ◽

Vol 27 (48) ◽

pp. no-no

Author(s):

T. KITAMURA ◽

T. FUKUOKA ◽

Y. FUJIWARA

Keyword(s):

N-C Aryl Transfer via Umpolung Carbolithiation of Vinyl Ureas

Synfacts ◽

10.1055/s-0030-1257749 ◽

2010 ◽

Vol 2010 (08) ◽

pp. 0929-0929

Keyword(s):

Fluoroalkylation of Imidazoles by Hypervalent Iodonium Salts

Organic Letters ◽

10.1021/ol802399z ◽

2008 ◽

Vol 10 (24) ◽

pp. 5565-5568 ◽

Cited By ~ 19

Author(s):

Changqing Lu ◽

Don VanDerveer ◽

Darryl D. DesMarteau

Keyword(s):

Trifluoromethanesulfonic Anhydride

2-Iodosylbenzoic acid activated by trifluoromethanesulfonic anhydride: efficient oxidant and electrophilic reagent for preparation of iodonium salts

New Journal of Chemistry ◽

10.1039/d1nj03787k ◽

2021 ◽

Author(s):

Akira Yoshimura ◽

Christopher Huss ◽

Akio Saito ◽

Tsugio Kitamura ◽

Viktor V Zhdankin

Keyword(s):

Electrophilic Reagent ◽

Iodonium Salts ◽

2-Iodosylbenzoic acid in the presence of trifluoromethanesulfonic anhydride is an efficient oxidant and electrophilic reagent useful for preparation of the corresponding alkenyl and aryliodonium salts. Compared to the previously reported...