Oxidative Coupling of Aryl Boron Reagents with sp3-Carbon Nucleophiles: The Enolate Chan-Evans-Lam Reaction

2016 ◽  
Vol 55 (5) ◽  
pp. 1894-1898 ◽  
Author(s):  
Patrick J. Moon ◽  
Heather M. Halperin ◽  
Rylan J. Lundgren
Keyword(s):  
Oxidative Coupling ◽  
Carbon Nucleophiles

Oxidative Coupling of Aryl Boron Reagents with sp3-Carbon Nucleophiles: The Enolate Chan-Evans-Lam Reaction

2016 ◽  
Vol 128 (5) ◽  
pp. 1926-1930 ◽  
Author(s):  
Patrick J. Moon ◽  
Heather M. Halperin ◽  
Rylan J. Lundgren
Keyword(s):  
Oxidative Coupling ◽  
Carbon Nucleophiles

Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles

Synlett ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 697-698 ◽  
Author(s):  
Tadakatsu Mandai ◽  
Hiroaki Kunitomi ◽  
Kiyoto Higashi ◽  
Mikio Kawada ◽  
Jiro Tsuji
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon

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

2019 ◽  
Author(s):  
Leiyang Lv ◽  
Dianhu Zhu ◽  
Zihang Qiu ◽  
Jianbin Li ◽  
Chao-Jun Li
Keyword(s):  
Catalytic Method ◽  
Unsaturated Hydrocarbons ◽  
Carbon Nucleophiles ◽  
Aryl Aldehydes ◽  
Aldehydes And Ketones ◽  
Sterically Hindered

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.

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