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Nickel-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Hydrazones

preprint
submitted on 12.06.2019 and posted on 13.06.2019 by Leiyang Lv, Dianhu Zhu, Zihang Qiu, Jianbin Li, Chao-Jun Li
Hydroalkylation of unsaturated hydrocarbons with unstablized carbon nucleophiles is difficult and remains a major challenge. The disclosed examples so far mainly focused on the involvement of heteroatom and/or stabilized carbon nucleophiles as efficient reaction partners. Reported here is an unprecedented regioselective nickel-catalyzed hydroalkylation of 1,3-dienes with hydrazones, generated in situ from abundant aryl aldehydes and ketones and acted as both the sources of unstabilized carbanions and hydride. With this strategy, both terminal and sterically hindered internal dienes are hydroalkylated efficiently in a highly selective manner, thus providing a novel and reliable catalytic method to construct challenging C(sp3)-C(sp3) bonds.

History

Email Address of Submitting Author

lvleiyang2008@gmail.com

Institution

McGill University

Country

Canada

ORCID For Submitting Author

0000-0002-2850-8952

Declaration of Conflict of Interest

The authors declare no competing financial interest

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