Technology for Organic Synthesis Department, Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russia.
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium.
J Org Chem. 2022 Sep 16;87(18):12274-12286. doi: 10.1021/acs.joc.2c01456. Epub 2022 Sep 1.
The reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles was examined in the Rh(II)-catalyzed transannulation reaction with nitriles. We have come across the interesting observation that 1-sulfonyl cycloalkeno[][1,2,3]triazoles that possess β-hydrogens resist intramolecular β-hydride migration and could serve as a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-, dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[]imidazoles were synthesized from various nitriles in good yields. A one-pot methodology has also been executed for the synthesis of -imidazoles.
我们考察了易得的 4,5-稠合-1-磺酰基-1,2,3-三唑在 Rh(II)催化的腈类化合物的交叉环化反应中的反应性。我们有一个有趣的发现，即具有β-氢的 1-磺酰基环烯[][1,2,3]三唑抵抗分子内β-氢迁移，并且可以作为用于分子间 Rh(II)催化交叉环化反应的新型 Rh-亚氨基卡宾源。结果，各种腈可高产合成得到 1-磺酰基环己烯、环庚烯、二氢吡喃、5-苯基四氢苯并和 4,5-二氢萘并[]咪唑。还执行了一锅法来合成-咪唑。
