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Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes

Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt(3), the Mi...

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Detalles Bibliográficos
Autores principales: Zhang, Wei-Song, Ji, Ding-Wei, Li, Ying, Zhang, Xiang-Xin, Mei, Yong-Kang, Chen, Bing-Zhi, Chen, Qing-An
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9902549/
https://www.ncbi.nlm.nih.gov/pubmed/36746964
http://dx.doi.org/10.1038/s41467-023-36237-1
Descripción
Sumario:Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt(3), the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl(2) catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives.