Nickel-Catalyzed Regioselective Hydrobenzylation of 1,3-Dienes with Hydrazones
journal contributionposted on 12.09.2019, 01:03 by Leiyang Lv, Dianhu Zhu, Zihang Qiu, Jianbin Li, Chao-Jun Li
Hydroalkylation of unsaturated hydrocarbons with unstabilized carbon nucleophiles is difficult and remains a major challenge. The disclosed examples so far have mainly focused on the involvement of heteroatom and/or stabilized carbon nucleophiles as efficient reaction partners. Reported here is an unprecedented regioselective nickel-catalyzed hydrobenzylation of 1,3-dienes with hydrazones, generated in situ from abundant aryl aldehydes and ketones and acting as both the sources of unstabilized carbanion equivalent and hydride. With this strategy, both terminal and sterically hindered internal dienes are hydroalkylated efficiently in a highly selective manner, thus providing a reliable catalytic method to construct challenging C(sp3)–C(sp3) bonds.
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hydrazonestericallyregioselective nickel-catalyzed hydrobenzylationdienehydrideinvolvementmannerhydrocarbonaryl aldehydesunstabilized carbanion equivalentsourceunstabilized carbon nucleophilesNickel-Catalyzed Regioselective HydrobenzylationstrategyterminalReportedreaction partnersmethodHydrazones Hydroalkylationcarbon nucleophilesheteroatomchallengeDieneketonehydroalkylatedbond