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Published By Georg Thieme Verlag Kg

1437-2096, 0936-5214

Synlett ◽  
2022 ◽  
Author(s):  
Linhong Zuo ◽  
Wusheng Guo

Functionalized ketones and their derivatives are very important building blocks in organic synthesis and material chemistry. The development of novel methodology for the chemo-, regio-, diastereo-, stereo- and enantioselective synthesis of functionalized ketones and their derivatives is the continuous endeavor of organic chemists. Herein we highlight the new approach that was recently initiated and developed by our group for the synthesis of (enantioenriched) ketones and related derivatives based on zwitterionic metal-enolate (ZME) chemistry.


Synlett ◽  
2022 ◽  
Author(s):  
Jaideep Saha ◽  
Chenna Jagadeesh ◽  
Biplab Mondal

Capitalizing on the propensity of 1, 2-amino group migration in γ-aminocyclopentenone with a suitable promoter, gem-diaryl equipped systems unfolded an unprecedented avenue for the Lewis acid promoted displacement of γ-aniline group with nucleophiles such as indole. Such transformation, besides providing a means for direct γ-functionalization of cyclopentenones, presented innumerable scope for β, γ-annulation. Various tailored indolo bis-nucleophiles were explored in the current study that rendered an array of indole alkaloid-like compounds in excellent yields and selectivity through one-pot operation. Analysis of collective experimental observation along with designed control experiments strongly suggested the possibility of a retro aza-Piancatelli rearrangement, which is hitherto unknown in the context. Such repertoire could find potential applications in the synthesis of complex assemblies from the Piancatelli rearrangement and related processes. 1. Introduction 2. Aza-Piancatelli rearrangement and related domino processes 3. An unprecedented aza-Piancatelli-templated strategy for polycyclic assemblies 4. Summary and Outlook


Synlett ◽  
2022 ◽  
Author(s):  
Yanbang Li ◽  
William Kopcha ◽  
Antonio Rodriguez-Fortea ◽  
Jianyuan Zhang

We explored the reactivity and substrate scope of the reactions among an alkyl isocyanide, an sp-hybridized reactant (i.e. alkyne or allene), and a carbon cage, as a new approach to functionalize fullerenes and metallofullerenes. This account summarizes the key findings in our recent published work, and some original data for the reaction involving an isocyanide, allenes, and metallofullerene Lu3N@C80.


Synlett ◽  
2022 ◽  
Author(s):  
Eva Bednářová ◽  
Logan R. Beck ◽  
Tomislav Rovis ◽  
Samantha L. Goldschmid ◽  
Katherine Xie ◽  
...  

AbstractThe use of low-energy deep-red (DR) and near-infrared (NIR) light to excite chromophores enables catalysis to ensue across barriers such as materials and tissues. Herein, we report the detailed photophysical characterization of a library of OsII polypyridyl photosensitizers that absorb low-energy light. By tuning ligand scaffold and electron density, we access a range of synthetically useful excited state energies and redox potentials.1 Introduction1.1 Scope1.2 Measuring Ground-State Redox Potentials1.3 Measuring Photophysical Properties1.4 Synthesis of Osmium Complexes2 Properties of Osmium Complexes2.1 Redox Potentials of Os(L)2-Type Complexes2.2 Redox Potentials of Os(L)3-Type Complexes2.3 UV/Vis Absorption and Emission Spectroscopy3 Conclusions


Synlett ◽  
2022 ◽  
Author(s):  
Birgit Esser ◽  
Jan S Wössner ◽  
Mathias Hermann

Conjugated nanohoops are excellent candidates to study structure-property relationships, as optoelectronic materials and as hosts for supramolecular chemistry. While carbon nanohoops containing aromatics are well studied, antiaromatic units had not been incorporated until recently by our group using dibenzo[a,e]pentalene (DBP). The non-alternant electronic character of the DBP units significantly influences the optoelectronic properties of such nanohoops. We herein summarize our synthetic strategies to DBP-containing nanohoops, their structural and electronic properties, chirality and host-guest chemistry. We demonstrate how incorporating antiaromatic units leads to unique properties and opens new synthetic avenues, making such nanohoops attractive as potential electronic materials.


Synlett ◽  
2022 ◽  
Author(s):  
Motoki Ito ◽  
Shigeo Sugiyama ◽  
Yui Hasegawa ◽  
Satomi Saito ◽  
Asami Onda ◽  
...  

AbstractThis study reports the development of Rh(II)-catalyzed N–N bond-forming reaction of amino acid derivatives or aliphatic amines to provide hydrazine derivatives through the combined use of Rh2(esp)2 and [(3,4-dimethoxyphenyl)sulfonylimino]-2,4,6-trimethylphenyliodinane (3,4-(MeO)2C6H3SO2N=IMes). This is the first report of N–H amination of aliphatic amines with metal–nitrene species.


Synlett ◽  
2022 ◽  
Author(s):  
Fan Wu ◽  
Wei Wang ◽  
Ken Yao

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C–S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.


Synlett ◽  
2022 ◽  
Author(s):  
Long Li ◽  
Long-Wu Ye ◽  
Yao-Hong Yan

AbstractOver the past two decades, catalytic alkyne alkoxylation-initiated Claisen rearrangement has proven to be a practical and powerful strategy for the rapid assembly of a diverse range of structurally complex molecules. The rapid development of Claisen rearrangements triggered by transition-metal-catalyzed alkyne alkoxylation has shown great potential in the formation of carbon–carbon bonds in an atom-economic and mild way. However, metal-free alkyne alkoxylation-triggered Claisen rearrangement has seldom been exploited. Recently, Brønsted acids such as HNTf2 and HOTf have been shown to be powerful activators that promote catalytic alkyne alkoxylation/Claisen rearrangement, leading to the concise and flexible synthesis of valuable compounds with high efficiency and atom economy. Recent advances on the Brønsted acid catalyzed alkyne alkoxylation/Claisen rearrangement are introduced in this Account, in which both intramolecular and intermolecular tandem reactions are discussed.


Synlett ◽  
2022 ◽  
Author(s):  
Hui Xiong ◽  
Adam T. Hoye

AbstractA synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt followed by hydrolytic decomposition of the pyridinium moiety to furnish the 2-aminopyridine product. The method is compatible with a wide range of functional groups, is scalable, and features inexpensive reagents. 15N-labeling results gave products consistent with a Zincke reaction mechanism.


Synlett ◽  
2022 ◽  
Author(s):  
Jing Jiao ◽  
Pengyang Wang ◽  
Fangtao Xiao ◽  
Zhipeng Zhang

Quinolines especially 2-aminoquinolines are highly important heterocycles in medicinal chemistry. 2-Aminoquinolines can be synthesized via stepwise construction of quinoline ring followed by additional amination, however the protocol is cumbersome. Herein, we describe a [5+1] cyclization of 2-vinylanilines with tetraalkylthiuram disulfide in the presence of iodine and copper(II) triflate. This reaction directly employs readily available and low-cost thiuram as both C1 synthon and nitrogen source, providing a facile approach for one-step synthesis of a variety of 2-aminoquinolines in good to excellent yields.


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