Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts via [3,3]-sigmatropic rearrangement

2020 ◽  
Vol 56 (59) ◽  
pp. 8226-8229
Author(s):  
Hairui Yuan ◽  
Yuanbo Du ◽  
Fengting Liu ◽  
Lirong Guo ◽  
Qianyu Sun ◽  
...  
Keyword(s):  
Sigmatropic Rearrangement ◽  
Diaryliodonium Salts

Tandem approach to NOBIN analogues from arthydroxylamines and diaryliodonium salts via [3,3]-sigmatropic rearrangement.

scholarly journals Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3223
Author(s):  
Ji-Wei Zhang ◽  
Shao-Hua Xiang ◽  
Shaoyu Li ◽  
Bin Tan
Keyword(s):  
Amino Alcohols ◽  
Sigmatropic Rearrangement ◽  
Synthetic Route ◽  
Mild Conditions ◽  
Good Substrate ◽  
Diaryliodonium Salts ◽  
Axially Chiral

NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

Synthesis of Non-C2 Symmetrical NOBIN-Type Biaryls Through a Cascade N-Arylation and [3,3]-Sigmatropic Rearrangement from O-Arylhydroxylamines and Diaryliodonium Salts

2021 ◽  
Author(s):  
Fengting Liu ◽  
Min Wang ◽  
Jiatong Qu ◽  
Haifeng Lu ◽  
Hongyin Gao
Keyword(s):  
Sigmatropic Rearrangement ◽  
Mild Conditions ◽  
Diaryliodonium Salts

We developed herein a regioselective construction of non-C2 symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts under mild conditions. The employment of copper...

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

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>

Cu-Catalyzed Cascade Reaction of Isoxazoles with Diaryliodonium Salts for the Synthesis of Acridines

2020 ◽  
Vol 17 (12) ◽  
pp. 944-950
Author(s):  
Shangrong Zhu ◽  
Xuechen Lu ◽  
Qiuneng Xu ◽  
Jian Li ◽  
Shenghu Yan
Keyword(s):  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Acridine Derivatives ◽  
Diaryliodonium Salts

A straightforward and efficient synthesis of acridine derivatives via a copper-catalyzed cascade reaction among isoxazoles and diaryliodonium salts is achieved. Various mono-, multi-substituted and 9-substituted acridine derivatives could be obtained in moderate to good yields. The process has gone through tandem double arylation and Friedel-Crafts reactions.

ChemInform Abstract: A Simple and Facile Heck-Type Arylation of Alkenes with Diaryliodonium Salts Using Magnetically Recoverable Pd-Catalyst.

ChemInform ◽  
2012 ◽  
Vol 43 (50) ◽  
pp. no-no
Author(s):  
Buchi Reddy Vaddula ◽  
Amit Saha ◽  
John Leazer ◽  
Rajender S. Varma
Keyword(s):  
Pd Catalyst ◽  
Diaryliodonium Salts

An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers

2021 ◽  
Author(s):  
Rahul N. Gaykar ◽  
Malini George ◽  
Avishek Guin ◽  
Subrata Bhattacharjee ◽  
Akkattu T. Biju
Keyword(s):  
Sigmatropic Rearrangement ◽  
Enol Ethers

scholarly journals Imino‐λ 3 ‐iodane and Catalytic Amount of I 2 ‐Mediated Synthesis of N ‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement

2020 ◽  
Vol 2020 (41) ◽  
pp. 6433-6439
Author(s):  
Cody L. Makitalo ◽  
Akira Yoshimura ◽  
Gregory T. Rohde ◽  
Irina A. Mironova ◽  
Rosa Y. Yusubova ◽  
...  
Keyword(s):  
Catalytic Amount ◽  
Sigmatropic Rearrangement

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

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