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Nickel-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Hydrazones
preprintsubmitted on 12.06.2019, 21:23 and posted on 13.06.2019, 15:08 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.