Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Rh(ii)-Catalyzed denitrogenative 1-sulfonyl-1,2,3-triazole-1-alkyl-1,2,3-triazole cross-coupling as a route to 3-sulfonamido-1H-pyrroles and 1,2,3-triazol-3-ium ylides. / Коронатов, Александр Николаевич; Афанасьева, Ксения Константиновна; Сахаров, Павел Алексеевич; Ростовский, Николай Витальевич; Хлебников, Александр Феодосиевич; Новиков, Михаил Сергеевич.
в: Organic Chemistry Frontiers, Том 8, № 7, 07.04.2021, стр. 1474-1481.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Rh(ii)-Catalyzed denitrogenative 1-sulfonyl-1,2,3-triazole-1-alkyl-1,2,3-triazole cross-coupling as a route to 3-sulfonamido-1H-pyrroles and 1,2,3-triazol-3-ium ylides
AU - Коронатов, Александр Николаевич
AU - Афанасьева, Ксения Константиновна
AU - Сахаров, Павел Алексеевич
AU - Ростовский, Николай Витальевич
AU - Хлебников, Александр Феодосиевич
AU - Новиков, Михаил Сергеевич
N1 - Publisher Copyright: © the Partner Organisations.
PY - 2021/4/7
Y1 - 2021/4/7
N2 - A method for the synthesis of 1-Alkyl-3-sulfonamido-1H-pyrroles by the Rh(ii)-catalyzed denitrogenative coupling of two different types of 1,2,3-Triazoles, 1-Alkyl-4-Aryl-and 1-sulfonyl-4-Aryl-1,2,3-Triazoles, has been developed. According to the DFT calculations, the reaction proceeds via the attack of the rhodium-bound azavinyl carbene, derived from the sulfonyl-1,2,3-Triazole, at the N2 atom of the 1-Alkyl-4-Aryl-1,2,3-Triazole and the successive formation of the rhodium-bound 1,2,3-Triazol-3-ium ylide, metal-free 1,2,3-Triazol-3-ium ylide, 1,4,5,8-Tetraazaocta-1,3,5,7-Tetraene, and 3-(azavinyl)-3,4-dihydro-1,2,4-Triazine. The concerted denitrogenative ring contraction of the latter followed by 1,2-prototropic shift affords the 1-Alkyl-3-sulfonamidopyrrole. This protocol provides 3-sulfonamidopyrroles from 1-Alkyl-4-Aryl-1,2,3-Triazoles in 24-91% yield. In contrast to 1-Alkyl-4-Aryl-1,2,3-Triazoles, 1,4-dialkyl-1,2,3-Triazoles under the same conditions afford stable 1,2,3-Triazol-3-ium ylides in 30-99% yield.
AB - A method for the synthesis of 1-Alkyl-3-sulfonamido-1H-pyrroles by the Rh(ii)-catalyzed denitrogenative coupling of two different types of 1,2,3-Triazoles, 1-Alkyl-4-Aryl-and 1-sulfonyl-4-Aryl-1,2,3-Triazoles, has been developed. According to the DFT calculations, the reaction proceeds via the attack of the rhodium-bound azavinyl carbene, derived from the sulfonyl-1,2,3-Triazole, at the N2 atom of the 1-Alkyl-4-Aryl-1,2,3-Triazole and the successive formation of the rhodium-bound 1,2,3-Triazol-3-ium ylide, metal-free 1,2,3-Triazol-3-ium ylide, 1,4,5,8-Tetraazaocta-1,3,5,7-Tetraene, and 3-(azavinyl)-3,4-dihydro-1,2,4-Triazine. The concerted denitrogenative ring contraction of the latter followed by 1,2-prototropic shift affords the 1-Alkyl-3-sulfonamidopyrrole. This protocol provides 3-sulfonamidopyrroles from 1-Alkyl-4-Aryl-1,2,3-Triazoles in 24-91% yield. In contrast to 1-Alkyl-4-Aryl-1,2,3-Triazoles, 1,4-dialkyl-1,2,3-Triazoles under the same conditions afford stable 1,2,3-Triazol-3-ium ylides in 30-99% yield.
UR - https://pubs.rsc.org/en/content/articlelanding/2021/qo/d0qo01571g#!divAbstract
UR - http://www.scopus.com/inward/record.url?scp=85103780510&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/79f90121-1d06-329a-aeae-6900ec789db7/
U2 - 10.1039/d0qo01571g
DO - 10.1039/d0qo01571g
M3 - Article
VL - 8
SP - 1474
EP - 1481
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
SN - 2052-4110
IS - 7
ER -
ID: 74409835