Metal-Free ipso-Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide

Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3758-3764 ◽  
Author(s):  
Sébastien Redon ◽  
Anne Roly Obah Kosso ◽  
Julie Broggi ◽  
Patrice Vanelle
Keyword(s):  
Selenium Dioxide ◽  
New Method ◽  
Metal Free ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Set Up

The first ipso-selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.

Direct and metal-free oxidative amination of sp3 C–H bonds for the construction of 2-hetarylquinazolin-4(3H)-ones

2016 ◽  
Vol 3 (9) ◽  
pp. 1096-1099 ◽  
Author(s):  
Huanhuan Liu ◽  
Tianran Zhai ◽  
Shiteng Ding ◽  
Yalei Hou ◽  
Xiangyu Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
New Method ◽  
Oxidative Amination ◽  
Metal Free ◽  
Mild Conditions

New method for synthesis of 2-hetarylquinazolin-4(3H)-ones from 2-aminobenzamides and (2-azaaryl)methanes under transition-metal free conditions, featuring a wide substrate scope with a broad range of functional group tolerance under mild conditions.

Green synthesis of diaryl selenides from arylboronic acids and arylseleninic acids.

Synlett ◽  
2022 ◽  
Author(s):  
Sebastien Redon ◽  
Vincent Remusat ◽  
Patrice Vanelle
Keyword(s):  
Green Synthesis ◽  
Environmentally Friendly ◽  
Present Approach ◽  
New Method ◽  
Free Base ◽  
Metal Free ◽  
Arylboronic Acids

A new method of deborylative selanylation using arylboronic acids and arylseleninic acids gave diaryl selenoethers and diarylselenoxide. The present approach requires only equimolar arylseleninic acid and led selectively to selenoethers or selenoxides depending on the solvent. The method is metal-free, base- or oxidant-free, efficient, and environmentally friendly.

A strategy for generating aryl radicals from arylborates through organic photoredox catalysis: photo-Meerwein type arylation of electron-deficient alkenes

2018 ◽  
Vol 54 (10) ◽  
pp. 1257-1260 ◽  
Author(s):  
Y. Iwata ◽  
Y. Tanaka ◽  
S. Kubosaki ◽  
T. Morita ◽  
Y. Yoshimi
Keyword(s):  
Photoredox Catalysis ◽  
Metal Free ◽  
Arylboronic Acids ◽  
Aryl Radicals ◽  
Mild Conditions

Generation of a variety of aryl radicals from arylboronic acids through metal-free photoredox catalysis under mild conditions.

ChemInform Abstract: Metal Free ipso Iodination of Arylboronic Acids Using CTAB/I2in Aqueous Media: Green and Regioselective Synthesis of Aryliodides under Mild Conditions.

ChemInform ◽  
2015 ◽  
Vol 46 (35) ◽  
pp. no-no
Author(s):  
Rajesh H. Tale ◽  
Gopal K. Toradmal ◽  
Venkatesh B. Gopula ◽  
Atish H. Rodge ◽  
Rajendra P. Pawar ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Regioselective Synthesis ◽  
Metal Free ◽  
Arylboronic Acids ◽  
Mild Conditions

Practical Transition-Metal-Free Protodeboronation of Arylboronic Acids in Aqueous Sodium Hypochlorite

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2039-2042
Author(s):  
Minxin Li ◽  
Yanling Tang ◽  
Zewei Mao ◽  
Jinchun Gao ◽  
Gaoxiong Rao
Keyword(s):  
Transition Metal ◽  
Sodium Hypochlorite ◽  
Low Cost ◽  
Practical Method ◽  
Aqueous Sodium ◽  
Metal Free ◽  
Arylboronic Acids ◽  
Mild Conditions

AbstractA concise and practical method was developed for the protodeboronation of arylboronic acids under mild conditions in aqueous NaClO at 100 °C. The strategy is low-cost, transition-metal-free, and base-free.

Metal free ipso iodination0 of arylboronic acids using CTAB/I2 in aqueous media: green and regioselective synthesis of aryliodides under mild conditions

2015 ◽  
Vol 56 (21) ◽  
pp. 2699-2703 ◽  
Author(s):  
Rajesh H. Tale ◽  
Gopal K. Toradmal ◽  
Venkatesh B. Gopula ◽  
Atish H. Rodge ◽  
Rajendra P. Pawar ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Regioselective Synthesis ◽  
Metal Free ◽  
Arylboronic Acids ◽  
Mild Conditions

A Sequential Ugi-Smiles / Transition-Metal-Free Endo-Dig Conia-ene Cyclization: The Selective Synthesis of Saccharin Substituted 2,5-dihydropyrroles

2021 ◽  
Author(s):  
Hassan Seyrani ◽  
Sorour Ramezanpour ◽  
Aref Vaezghaemi ◽  
Farzad Kobarfard
Keyword(s):  
Transition Metal ◽  
Free Access ◽  
Selective Synthesis ◽  
Metal Free ◽  
Mild Conditions

A convenient, transition-metal-free access to a series of unprecedented saccharin substituted 2,5-dihydropyrroles is reported. This approach employs a post-Ugi-Smiles 5-endo-dig Conia-ene cyclization sequence in mild conditions while incorporating a series...

Metal‐free direct oxidative C–N bond coupling of quinoxalin‐2(1H)‐ones with azoles under mild conditions

2021 ◽  
Author(s):  
Jingwen Guo ◽  
Lina Zhang ◽  
Xinyue Du ◽  
Liting Zhang ◽  
Yuepiao Cai ◽  
...  
Keyword(s):  
Metal Free ◽  
Mild Conditions

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

scholarly journals An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade

2021 ◽  
Author(s):  
Philipp Natho ◽  
Zeyu Yang ◽  
Lewis Allen ◽  
Juliette Rey ◽  
Andrew J P White ◽  
...  
Keyword(s):  
Transition Metal ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles....

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