638538-20-2Relevant academic research and scientific papers
Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation
Chu, Crystal K.,Ziegler, Daniel T.,Carr, Brian,Wickens, Zachary K.,Grubbs, Robert H.
supporting information, p. 8435 - 8439 (2016/07/19)
An aldehyde-selective Wacker-type oxidation of allylic fluorides proceeds with a nitrite catalyst. The method represents a direct route to prepare β-fluorinated aldehydes. Allylic fluorides bearing a variety of functional groups are transformed in high yield and very high regioselectivity. Additionally, the unpurified aldehyde products serve as versatile intermediates, thus enabling access to a diverse array of fluorinated building blocks. Preliminary mechanistic investigations suggest that inductive effects have a strong influence on the rate and regioselectivity of the oxidation.
Iridium-catalyzed allylic fluorination of trichloroacetimidates
Topczewski, Joseph J.,Tewson, Timothy J.,Nguyen, Hien M.
, p. 19318 - 19321 (2012/01/06)
A rapid allylic fluorination method utilizing trichloroacetimidates in conjunction with an iridium catalyst has been developed. The reaction is conducted at room temperature under ambient air and relies on Et 3N?3HF reagent to provide branched allylic fluorides with complete regioselectivity. This high-yielding reaction can be conducted on a multigram scale and shows considerable functional group tolerance. The use of [18F]KF?Kryptofix allowed 18F- incorporation in 10 min.
Fluorous synthesis of allylic fluorides: C-F bond formation as the detagging process
Boldon, Sophie,Moore, Jane E.,Gouverneur, Veronique
supporting information; experimental part, p. 3622 - 3624 (2009/02/05)
A novel fluorous tagging-detagging strategy has been developed featuring a fluorination as the detagging process; fluorous allylsilanes were prepared by cross-metathesis and subsequently subjected to electrophilic fluorodesilylation; Selectfluor was used as the detagging reagent; the resulting allylic fluorides were successfully purified by fluorous solid phase extraction. The Royal Society of Chemistry.
Sequential Cross-Metathesis/ Electrophilic Fluorodesilylation: A Novel Entry to Functionalized Allylic Fluorides
Thibaudeau, Sebastien,Gouverneur, Veronique
, p. 4891 - 4893 (2007/10/03)
(Equation Presented) Various allylic fluorides were prepared using a two-step process involving a cross-metathesis of allyltrimethylsilane with different olefinic partners followed by a fluorodesilylation of the corresponding functionalized allylsilanes w
