Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature; Chemistry - A European Journal; Vol. 23, iss. 66
| Parent link: | Chemistry - A European Journal Vol. 23, iss. 66.— 2017.— [P. 16738–16742] |
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| Korporacja: | |
| Kolejni autorzy: | , , , , , , , , , |
| Streszczenie: | Title screen New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 Е between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields. Режим доступа: по договору с организацией-держателем ресурса |
| Język: | angielski |
| Wydane: |
2017
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| Hasła przedmiotowe: | |
| Dostęp online: | http://dx.doi.org/10.1002/chem.201704393 |
| Format: | Elektroniczne Rozdział |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=656722 |
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| 200 | 1 | |a Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature |f A. Yoshimura [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: p. 16741-16742 (16 tit.)] | ||
| 330 | |a New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 Е between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Chemistry - A European Journal | ||
| 463 | |t Vol. 23, iss. 66 |v [P. 16738–16742] |d 2017 | ||
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| 701 | 1 | |a Fuchs |b Jo. M. |g Jonathan | |
| 701 | 1 | |a Middleton |b K. R. |g Kyle | |
| 701 | 1 | |a Maskaev |b A. V. |g Andrey | |
| 701 | 1 | |a Rohde |b G. T. |g Gregory | |
| 701 | 1 | |a Saito |b A. |g Akio | |
| 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 | |
| 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 | |
| 701 | 1 | |a Nemykin |b V. N. |g Viktor Nikolaevich | |
| 701 | 1 | |a Zhdankin |b V. V. |c химик |c Professor of Tomsk Polytechnic University, Doctor of chemical sciences |f 1956- |g Viktor Vladimirovich |3 (RuTPU)RU\TPU\pers\35758 | |
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