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

ABSTRACT: 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/NEt₃, the Mizoroki-Heck reaction of dienes delivers linear products under Ni(dppe)Cl₂ 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.

SUBMITTER: Zhang WS

PROVIDER: S-EPMC9902549 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Zhang Wei-Song WS Ji Ding-Wei DW Li Ying Y Zhang Xiang-Xin XX Mei Yong-Kang YK Chen Bing-Zhi BZ Chen Qing-An QA

Nature communications 20230206 1

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<sub>3</sub>, the Mizoroki-Heck reaction of dienes delivers linear products under Ni(dppe)Cl<sub>2</sub> catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF ...[more]

PMID: 36746964

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