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Novel Metal-mediated (M = Pd, Pt) coupling between isonitriles and benzophenone hydrazone as a route to aminocarbene complexes exhibiting high catalytic activity (M = Pd) in the Suzuki-Miyaura reactionстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 20 апреля 2022 г.
- Авторы: Luzyanin K.V., Tskhovrebov A.G., Carolina Carias M., Fátima Guedes C.Da Silva M, Pombeiro A.J.L, Kukushkin V.Yu
- Журнал: Organometallics
- Том: 28
- Номер: 22
- Год издания: 2009
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 6559
- Последняя страница: 6566
- DOI: 10.1021/om900682v
- Аннотация: Metal-mediated reaction between equimolar amounts of CW-[MCl 2(C=NR)2] [M = Pd, R = cyclohexyl (Cy) 1, Bu 2,2,6-Me 2C6H3 (XyI) 3,4-MeOC6H4 4; M = Pt, R = cyclohexyl (Cy) 5,2,6Me2CeH3 (XyI) 7,4-MeOC6H4 8] and benzophenone hydrazone, H 2N-N=CPn2, proceeds in CHCl3 under reflux for 8 h. The subsequent workup provides the carbene species c/s-[MCl 2C(N(H)N= CPh2)=N(H)R(C=NR)] (M = Pd, 9-12; M = Pt, 13-15) in good (80-85%) isolated yields. Complexes 9-15 are air- and moisture-stable in the 20-80 °C temperature range and were characterized by elemental analyses (C, H, N), ESI+-MS, IR, and ID (1H, 13C(1H)) and 2D (1HV1H-COSY, 1H, 13C-HMQC/1H, 13C-HSQC, 1H, 13C-HMBC) NMR spectroscopies. In addition, the structures of two metallacarbenes, 11 and 14, were elucidated by single-crystal X-ray diffraction. The catalytic properties of 9-15 in the Suzuki-Miyaura cross-coupling of the aryl bromides 4-R2C6H4Br (R2 = H, Me, OMe, and NO2) with phenylboronic acid (in EtOH as a solvent, K2CO3 as a base, 80 °C), yielding biaryl species, were evaluated, and it was found that the palladiumaminocarbene species 9-12 exhibit a high catalytic activity (yields up to 97%, TONs up to 1.4 × 106). © 2009 American Chemical Society.
- Добавил в систему: Цховребов Александр Георгиевич