Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions

2002 ◽  
Vol 1 (2) ◽  
pp. 254-256 ◽  
Author(s):  
Okiko Miyata ◽  
Norihiko Takeda ◽  
Yoshiaki Morikami ◽  
Takeaki Naito
Keyword(s):  
Sigmatropic Rearrangement ◽  
Mild Conditions

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...

Efficient [3,3]-Sigmatropic Rearrangement Accelerated by a Trifluoroacetyl Group: Synthesis of Benzofurans under Mild Conditions.

ChemInform ◽  
2003 ◽  
Vol 34 (22) ◽  
Author(s):  
Okiko Miyata ◽  
Norihiko Takeda ◽  
Yoshiaki Morikami ◽  
Takeaki Naito
Keyword(s):  
Sigmatropic Rearrangement ◽  
Mild Conditions

Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement

2018 ◽  
Vol 54 (47) ◽  
pp. 6036-6039 ◽  
Author(s):  
Meng-Guang Zhou ◽  
Rui-Han Dai ◽  
Shi-Kai Tian
Keyword(s):  
Nucleophilic Addition ◽  
Conjugated Dienes ◽  
Sigmatropic Rearrangement ◽  
Mild Conditions ◽  
Convenient Access

Treatment of tertiary propargylic amines with 2-(trimethylsilyl)aryl triflates under mild conditions provides convenient access to amino-substituted allenes or conjugated dienes.

The Diorgano Dichalcogenides Addition to Benzyne under Mild Conditions

2007 ◽  
Author(s):  
Fabiano Toledo ◽  
Henrique Marques ◽  
João Comasseto ◽  
Cristiano Raminelli
Keyword(s):  
Mild Conditions

Pt-Pd Nanoalloy for the Unprecedented Activation of Carbon-Fluorine Bond at Low Temperature

2019 ◽  
Author(s):  
Raghu Nath Dhital ◽  
keigo nomura ◽  
Yoshinori Sato ◽  
Setsiri Haesuwannakij ◽  
Masahiro Ehara ◽  
...  
Keyword(s):  
Activation Energy ◽  
Low Temperature ◽  
Dft Calculations ◽  
Bond Activation ◽  
Mild Conditions ◽  
Selective Transformation ◽  
Rate Determining Step ◽  
Highly Active ◽  
Harsh Conditions ◽  
Reaction Profile

Carbon-Fluorine (C-F) bonds are considered the most inert organic functionality and their selective transformation under mild conditions remains challenging. Herein, we report a highly active Pt-Pd nanoalloy as a robust catalyst for the transformation of C-F bonds into C-H bonds at low temperature, a reaction that often required harsh conditions. The alloying of Pt with Pd is crucial to activate C-F bond. The reaction profile kinetics revealed that the major source of hydrogen in the defluorinated product is the alcoholic proton of 2-propanol, and the rate-determining step is the reduction of the metal upon transfer of the <i>beta</i>-H from 2-propanol. DFT calculations elucidated that the key step is the selective oxidative addition of the O-H bond of 2-propanol to a Pd center prior to C-F bond activation at a Pt site, which crucially reduces the activation energy of the C-F bond. Therefore, both Pt and Pd work independently but synergistically to promote the overall reaction

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

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