71813-51-9

Usage

Chemical compound

4-(2-Fluorophenyl)-1-butene

Class of compounds

Phenylbutenes

Molecular weight

150.194 g/mol

Density

1.04 g/cm3

Primary use

Scientific research and synthesis of other organic compounds

Caution

Handle with care due to potential hazardous effects on human health and the environment

InChI:InChI=1/C10H11F/c1-2-3-6-9-7-4-5-8-10(9)11/h2,4-5,7-8H,1,3,6H2

Upstream product

• 24892-64-6 1-(but-3-en-1-yl)-2-iodobenzene 
• 591-87-7 Allyl acetate 
• 401514-50-9 o-fluorobenzaldehyde hydrazone 
• 76727-24-7 3-(2-fluorophenyl)propan-1-ol 
• 1643-26-1 3-(2-fluorophenyl)propionic acid 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 175143-93-8 3-(2-fluorophenyl)propanal 
• 446-52-6 2-Fluorobenzaldehyde 
• 446-48-0 o-fluorobenzyl bromide 
• 2622-05-1 allylmagnesium bromide 
• 107616-48-8 2-(but-3-en-1-yl)benzenediazonium hexafluorophosphate 
• 6992-97-8 2-(but-3-en-1-yl)aniline 
• 102330-20-1 1-(but-3-en-1-yl)-2-nitrobenzene 
• 274676-13-0 methyl (+/-)-2-(2-nitrophenyl)-4-pentenoate 

Downstream Products

• 767-58-8 1-methylindane 
• 768-56-9 4-Phenylbut-1-ene 

Relevant academic research and scientific papers

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Copper-mediated fluorination of aryl iodides

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.