779357-32-3

Basic information

• Product Name: 1,3,5-tris((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzene
• Synonyms: 1,3,5-tris((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzene
• CAS NO: 779357-32-3
• Molecular Weight: 534.117
• Mol File: 779357-32-3.mol

Chemical Properties

• CAS DataBase Reference: 1,3,5-tris((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-tris((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzene(779357-32-3)
• EPA Substance Registry System: 1,3,5-tris((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzene(779357-32-3)

Safety Data

• Hazardous Substances Data: 779357-32-3(Hazardous Substances Data)

Upstream product

• 7567-63-7 1,3,5-Triethynylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

Stereoselective hydroboration of diynes and triyne to give products containing multiple vinylene bridges: A versatile application to fluorescent dyes and light-emitting copolymers

The Rh(I)-catalyzed hydroboration of a variety of aromatic diynes and a triyne afforded bis(boryl)- and tris(boryl)vinyl products. The hydroboration products underwent Suzuki cross-coupling reactions with a variety of substrates containing chromophore units to give fluorescent dye-substituted products. The hydroboration product also reacted with dibromoarenes to afford an oligomer with a vinylene unit along the oligomer backbone.

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.

AgSbF6-Catalyzed: Anti -Markovnikov hydroboration of terminal alkynes

AgSbF6-Catalyzed anti-Markovnikov addition of pinacolborane (HBpin) to terminal alkynes to produce the E-vinylboronates is reported. This efficient methodology is scalable, compatible with sterically and electronically diverse alkynes, and works at room temperature under solvent-free condition. The utility of this method is demonstrated in the facile synthesis of the clinically important (E)-2,4,3′,5′-tetramethoxystilbene.