Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts; Advanced Synthesis and Catalysis; Vol. 363, iss. 14
| Parent link: | Advanced Synthesis and Catalysis Vol. 363, iss. 14.— 2021.— [P. 3566-3576] |
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| مؤلفون آخرون: | , , , , , , , , |
| الملخص: | Заглавие с экрана Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-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(3H)-ones and 1,2,4-oxadiazole-5-thiol. |
| اللغة: | الإنجليزية |
| منشور في: |
2021
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| الموضوعات: | |
| الوصول للمادة أونلاين: | https://doi.org/10.1002/adsc.202100426 |
| التنسيق: | MixedMaterials الكتروني فصل الكتاب |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=666040 |
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| 200 | 1 | |a Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts |f N. S. Soldatova, A. V. Semenov, K. K. Geyl [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Заглавие с экрана | ||
| 320 | |a [References: 74 tit.] | ||
| 330 | |a Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-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(3H)-ones and 1,2,4-oxadiazole-5-thiol. | ||
| 461 | |t Advanced Synthesis and Catalysis | ||
| 463 | |t Vol. 363, iss. 14 |v [P. 3566-3576] |d 2021 | ||
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a арилирование | |
| 701 | 1 | |a Soldatova |b N. S. |c organic chemist |c engineer of Tomsk Polytechnic University |f 1992- |g Nataliya Sergeevna |3 (RuTPU)RU\TPU\pers\36289 |9 19363 | |
| 701 | 1 | |a Semenov |b A. V. |g Artem Valerjevich |f 1997- |c Chemist |c Research Engineer of Tomsk Polytechnic University |y Tomsk |7 ba |8 eng |9 89056 | |
| 701 | 1 | |a Geyl |b K. K. |g Kirill Konstantinovich | |
| 701 | 1 | |a Baykov |b S. V. |c chemist |c Researcher at Tomsk Polytechnic University, Candidate of Chemical Sciences |f 1987- |g Sergey Valentinovich |3 (RuTPU)RU\TPU\pers\47276 |9 22856 | |
| 701 | 1 | |a Shetnev |b A. |g Anton | |
| 701 | 1 | |a Konstantinova |b A. S. |g Anna Sergeevna | |
| 701 | 1 | |a Korsakov |b M. K. |g Mikhail Konstantinovich | |
| 701 | 1 | |a Yusubov |b M. S. |c chemist |c Professor of Tomsk Polytechnic University, Doctor of chemical sciences |f 1961- |g Mekhman Suleiman-Ogly (Suleimanovich) |3 (RuTPU)RU\TPU\pers\31833 |9 15928 | |
| 701 | 1 | |a Postnikov |b P. S. |c organic chemist |c Associate Professor of Tomsk Polytechnic University, Candidate of chemical sciences |f 1984- |g Pavel Sergeevich |3 (RuTPU)RU\TPU\pers\31287 |9 15465 | |
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| 856 | 4 | |u https://doi.org/10.1002/adsc.202100426 | |
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