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...

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.

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

scholarly journals Hypervalent Iodine in Synthesis Part 39. Palladium-catalyzed Carbonylative Coupling of lodonium Salts and Potassium Aryltrifluoroborates by Carbon Monoxide

1999 ◽  
Vol 23 (6) ◽  
pp. 400-401
Author(s):  
Min Xia ◽  
Zhenchu Chen
Keyword(s):  
Carbon Monoxide ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Diaryliodonium Salts ◽  
Palladium Catalyzed

Diaryl ketones and chalcones are obtained in good yields by palladium-catalyzed carbonylative coupling of diaryliodonium salts and ( E)-phenylethenyl(phenyl)iodonium tetrafluoroborates with potassium aryltrifluoroborates in an atmosphere of carbon monoxide under mild conditions.

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 Selective Arylation of Oxadiazolones by Diaryliodonium Salts

2021 ◽  
Author(s):  
Natalia Soldatova ◽  
Artem Semenov ◽  
Kirill Geyl ◽  
Sergey Baykov ◽  
Anton Shetnev ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Structural Study ◽  
High Potential ◽  
Steric Effects ◽  
Mild Conditions ◽  
Diaryliodonium Salts ◽  
Steric Accessibility ◽  
Sterically Hindered ◽  
High Yields ◽  
Synthetic Application

The direct N-arylation of cyclic amides can be considered a pivotal issue for modern organic chemistry. Here, we report the method for copper-catalyzed <i>N</i>-arylation of diverse oxadiazolones by diaryliodonium salts in mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows to efficiently utilize both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). The evaluation of steric effects in aryl moieties to the chemoselectivity of <i>N</i>- and <i>O</i>-arylation of the 1,2,4-oxadiazol-5(4<i>H</i>)-ones exhibited the high potential of mesityl-substituted diaryliodonium salts as a selective arylation reagent. The structural study suggests that steric accessibility of <i>N</i>-atom in 1,2,4-oxadiazol-5(4<i>H</i>)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3<i>H</i>)-ones and 1,2,4-oxadiazole-5-thiol.

scholarly journals Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 483 ◽  
Author(s):  
Alexandra Pacheco-Benichou ◽  
Thierry Besson ◽  
Corinne Fruit
Keyword(s):  
Transition Metal ◽  
Structural Diversity ◽  
Complex Molecules ◽  
Mild Conditions ◽  
Diaryliodonium Salts ◽  
Selective Incorporation ◽  
C And N ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Complementary Strategy

Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners.

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

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.

scholarly journals Copper-Catalyzed Selective Arylation of Oxadiazolones by Diaryliodonium Salts

2021 ◽  
Author(s):  
Natalia Soldatova ◽  
Artem Semenov ◽  
Kirill Geyl ◽  
Sergey Baykov ◽  
Anton Shetnev ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Structural Study ◽  
High Potential ◽  
Steric Effects ◽  
Mild Conditions ◽  
Diaryliodonium Salts ◽  
Steric Accessibility ◽  
Sterically Hindered ◽  
High Yields ◽  
Synthetic Application

The direct N-arylation of cyclic amides can be considered a pivotal issue for modern organic chemistry. Here, we report the method for copper-catalyzed <i>N</i>-arylation of diverse oxadiazolones by diaryliodonium salts in mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows to efficiently utilize both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). The evaluation of steric effects in aryl moieties to the chemoselectivity of <i>N</i>- and <i>O</i>-arylation of the 1,2,4-oxadiazol-5(4<i>H</i>)-ones exhibited the high potential of mesityl-substituted diaryliodonium salts as a selective arylation reagent. The structural study suggests that steric accessibility of <i>N</i>-atom in 1,2,4-oxadiazol-5(4<i>H</i>)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3<i>H</i>)-ones and 1,2,4-oxadiazole-5-thiol.

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