67700-23-6Relevant academic research and scientific papers
Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling
Gurak, John A.,Engle, Keary M.
, p. 8987 - 8992 (2018/09/11)
The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.
A stereoselective approach to γ-functionalized carbonyls exploiting the Cu-promoted SN2′ reaction
Bond, Eric,Beausoleil, Anne-Marie,Howell, Jennifer,Wong, Alicia,Robichaud, Joel
experimental part, p. 2488 - 2493 (2011/06/24)
While several efficient processes exist to effect the stereoselective creation of carbon-carbon bonds in the α- and β-position of carbonyls, functionalization of the γ-position is much more challenging. We disclose an alternative methodology exploiting the Cu-promoted S N2′ reaction to achieve the addition of various nucleophiles upon the allylic lactones 5a-d which lead to the generation of the desired γ-functionalized α,β-unsaturated aldehydes 6 following in situ hydrolysis.
