60806-00-0

Upstream product

• 591-50-4 iodobenzene 
• 4627-10-5 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane 
• 624-31-7 4-tolyl iodide 
• 603-35-0 triphenylphosphine 
• 696-62-8 para-iodoanisole 
• 10199-14-1 4,4,6-trimethyl-1,3,2-dioxaborinane 
• 536-74-3 phenylacetylene 
• 230299-21-5 4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 107-41-5 2-methyl-2,4-pentanediol 
• 7568-01-6 2-butoxy-4,4,6-trimethyl-[1,3,2]dioxaborinane 
• 30094-01-0 β-styrylmagnesium bromide 

Downstream Products

• 1246746-46-2 N-benzyl-N-(1-cyclohexyl-3-phenylallyl)hydroxylamine 
• 1246746-41-7 N-benzyl-N-(1,3-diphenylallyl)hydroxylamine 
• 1246746-47-3 1-styryl-3,4-dihydro-1H-isoquinolin-2-ol 
• 57918-63-5 (Z)-styryl iodide 
• 42599-24-6 E-styryl iodide 
• 17329-15-6 1,6-diphenyl-1,3,5-hexatriene 
• 170080-16-7 (1Z,3E,5Z)-1,6-diphenylhexa-1,3,5-triene 
• 38557-34-5 cis,trans,trans-1,6-Diphenyl-1,3,5-hexatriene 

Relevant academic research and scientific papers

Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a C1-C7 Z,Z,E,-triene synthon for viridenomycin

Mechanistic studies of the Heck-Mizoroki reaction of a vinylboronate ester with electronically different (four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstrating that the oxidative addition step is not rate d

Transborylation of alkenylboranes with diboranes

Exchange of boryl moieties between alkenylboranes and diboron reagents has been postulated as a stereospecific cross-metathesis pathway with concomitant formation of mixed diboron reagents. DFT calculations propose a mechanism for the stereocontrolled C(sp2)-B/B′-B′ cross-metathesis with both symmetric and non-symmetric diboron reagents. This journal is

Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters

Vinylboronic esters derived from 4,4,6-trimethyl-[1,3,2]dioxaborinane react with nitrones in the presence of dimethylzinc; nucleophilic addition of the vinyl group onto nitrones produces N-allylic hydroxylamines in fair yields. The sequence is compatible with various functional groups on the vinylic moiety. The mechanism and kinetic aspects are discussed on the basis of DFT calculations.

Methylpentanediolborane: Easy access to new air- and chromatography-stable, highly functionalized vinylboronates

(Chemical Equation Presented) Methylpentanediolborane (MPBH) 1 can be prepared easily by reaction of hexyleneglycol with BH3/ DMS or B 2H6 generated from NaBH4 and I2. MPBH hydroborates stereo- and re

A stereoselective synthesis of 1,6-diphenyl-1,3,5-hexatrienes utilising 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane as a two-carbon alkenyl building block

A number of 1,6-diphenyl-1,3,5-hexatrienes of varying alkene geometries were stereoselectively prepared from just two starting materials: iodobenzene and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane via a series of Heck, Suzuki-Miyaura and stereocontrolled iododeboronation reactions. These results demonstrate how 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane can be used as a genuine two-carbon vinyl-dianion building block in stereocontrolled polyene synthesis. The Royal Society of Chemistry 2005.

4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: A superior 2-carbon building block for vinylboronate Heck couplings

4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane is a superior reagent in terms of stability and reactivity in comparison to the vinylboronate pinacol ester, giving improved selectivity for Heck versus Suzuki coupling with both aryl iodides and bromides, and being easier to prepare and store.