1433901-09-7

Basic information

• Product Name: (E)-2-(3-(4-(tert-butyl)phenyl)allyl)benzonitrile
• Synonyms: (E)-2-(3-(4-(tert-butyl)phenyl)allyl)benzonitrile
• CAS NO: 1433901-09-7
• Molecular Weight: 275.393
• Mol File: 1433901-09-7.mol

Chemical Properties

• CAS DataBase Reference: (E)-2-(3-(4-(tert-butyl)phenyl)allyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(3-(4-(tert-butyl)phenyl)allyl)benzonitrile(1433901-09-7)
• EPA Substance Registry System: (E)-2-(3-(4-(tert-butyl)phenyl)allyl)benzonitrile(1433901-09-7)

Safety Data

• Hazardous Substances Data: 1433901-09-7(Hazardous Substances Data)

Upstream product

• 1746-23-2 4-tert-Butylstyrene 
• 22115-41-9 2-(bromomethyl)benzonitrile 

Relevant articles and documents

Copper-catalysed direct radical alkenylation of alkyl bromides

A copper-catalysed direct radical alkenylation of various benzyl bromides and α-carbonyl alkyl bromides has been developed. Compared with the recent radical alkenylations which mostly focused on secondary or tertiary alkyl halides, this transformation shows good reactivity to primary alkyl halides and tertiary, secondary alkyl halides were also tolerated. The key initiation step of this transformation is a copper-induced single-electron reduction of C-Br bonds to generate alkyl radical species. This journal is the Partner Organisations 2014.

Visible-light photocatalytic radical alkenylation of a-carbonyl alkyl bromides and benzyl bromides

Through the use of [Ru- (bpy)3Cl2] (bpy=2,2'-bipyridine) and [Ir(ppy)3] (ppy=phenylpyridine) as photocatalysts, we have achieved the first example of visible-light photocatalytic radical alkenylation of various acarbonyl alkyl bromides and benzyl bromides to furnish a-vinyl carbonyls and allylbenzene derivatives, prominent structural elements of many bioactive molecules. Specifically, this transformation is regiospecific and can tolerate primary, secondary, and even tertiary alkyl halides that bear b-hydrides, which can be challenging with traditional palladium-catalyzed approaches. The key initiation step of this transformation is visible-light-induced single-electron reduction of CBr bonds to generate alkyl radical species promoted by photocatalysts. The following carboncarbon bond-forming step involves a radical addition step rather than a metal-mediated process, thereby avoiding the undesired b-hydride elimination side reaction. Moreover, we propose that the Ru and Ir photocatalysts play a dual role in the catalytic system: they absorb energy from the visible light to facilitate the reaction process and act as a medium of electron transfer to activate the alkyl halides more effectively. Overall, this photoredox catalysis method opens new synthetic opportunities for the efficient alkenylation of alkyl halides that contain b-hydrides under mild conditions.