1301266-96-5

Basic information

• Product Name: 4-fluorophenylvinylboronic acid
• Synonyms: 4-fluorophenylvinylboronic acid
• CAS NO: 1301266-96-5
• Molecular Weight: 165.96
• Mol File: 1301266-96-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-fluorophenylvinylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluorophenylvinylboronic acid(1301266-96-5)
• EPA Substance Registry System: 4-fluorophenylvinylboronic acid(1301266-96-5)

Safety Data

• Hazardous Substances Data: 1301266-96-5(Hazardous Substances Data)

Upstream product

• 850567-55-4 2-(1-(4-fluorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 350-35-6 1-(1,2-dibromoethyl)-4-fluorobenzene 
• 405-99-2 para-fluorostyrene 

Downstream Products

• 1621387-07-2 2-((1-(4-fluorophenyl)vinyl)oxy)isoindoline-1,3-dione 
• 1449377-22-3 C₁₃H₁₃BFNO₄ 
• 345-83-5 4-fluorobenzophenone 
• 1414852-71-3 MIDA ((4-fluorophenyl)oxomethyl)boronate 
• 345-89-1 4-fluoro-4'-methoxybenzophenone 
• 54978-50-6 4-cyanophenyl(4-flourophenyl)methanone 

Relevant articles and documents

Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations

Recent methodological reports for synthesizing acyl-MIDA boronate esters compel an investigation of their potential use as substrates in a standard Suzuki-Miyaura cross-coupling reaction. Here we report the production of benzophenones by C[sbnd]C cross coupling between a benzoyl-MIDA boronate ester and a multitude of aryl bromide substrates in adequate yields following optimization under ambient conditions outside of a glove box. Under these standard conditions, none of several acyl-MIDA boronate esters (in an alkyl series) serves as a competent coupling partner. The substrate scope is also limited by the finding that the corresponding trifluoroborates of both acyl- and aroyltrifluroborates are not suitable substrates. For reasons of availability and synthetic difficulty in procuring other aroyl-MIDA boronates, this preliminary study examines the reactivity of benzoyl-MIDA boronate with several aryl bromide substrates.

Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: Directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.

Intermolecular Carboamination of Unactivated Alkenes

Herein, we report the first example of group transfer radical addition of O-vinylhydroxylamine derivatives onto unactivated alkenes. By utilizing O-vinylhydroxylamine derivatives as both the N- and C-donors, this reaction enables intermolecular carboamination of unactivated alkenes in an atom economical fashion. As the process is initiated through N-radical addition followed by C-transfer, linear carboamination products are afforded. This differs from canonical radical carbofunctionalization of olefins, which typically favors branched product owing to initiation by C-radical addition.