15619-51-9

Upstream product

• 7217-01-8 trivinyl borane 
• 2288-18-8 2-phenyl-1,3-butadiene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 129493-14-7 9-vinyl-9-borabicyclo<3.3.1>nonane 
• 51171-71-2 4-phenyl-3-cyclohexen-1-one 
• 15619-38-2 4-Benzoyloxy-1-phenyl-cyclohexen-⁽¹⁾ 
• 51171-73-4 4-hydroxy-4-phenylcyclohexanone 
• 1079-68-1 2-bromo-4-phenylcyclohexanone 
• 3262-89-3 triphenylboroxine 
• 13482-22-9 4-hydroxycyclohexanone 
• 98-81-7 1-bromovinylbenzene 
• 75927-49-0 pinacol vinylboronate 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 100-42-5 styrene 

Downstream Products

• 15619-32-6 1-phenyl-cyclohexa-1,3-diene 
• 13703-52-1 1-phenyl-1,4-cyclohexadiene 
• 15619-39-3 O-(4-Phenyl-3-cyclohexenyl-⁽¹⁾)-S-methylxanthat 

Relevant academic research and scientific papers

Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes

A method for the stereoselective [4+2]-cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N-protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C?B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo phile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions

Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.

Vinylboranes are Omniphilic Dienophiles. Some Unusual and Useful Properties of Vinylboranes in Diels-Alder Reactions

The rate of Diels-Alder reactions with vinyl-9-BBN is uniquely insensitive to diene substituent effects, and high reactivity is observed with both electron-rich and electron-poor dienes.The regioselectivity of these reactions is controlled mainly by steric effects.

Tuning of vinylborane dienophilicity. Optimization of reactivity, regioselectivity, endo stereoselectivity, and reagent stability

Simple syntheses of some vinylboranes are reported, and their properties in Diels-Alder reactions are compared. Vinyl-3,6-dimethylborepane was the most stable simple vinylborane examined, and appears to be indefinitely stable at 25°C. Surprisingly, trivinylborane is the most reactive, and reacts about 18 times faster than the vinyldialkylboranes with cyclopentadiene. Vinyl-9-BBN is the most regioselective dienophile, in keeping with principally steric control of regioselectivity in Diels-Alder reactions of vinylboranes. All the dienophiles display high endo-stereoselectivity with piperylene, but vinyl-3,6-dimethylborepane displays significantly improved stereoselectivity with cyclopentadiene. In general, by choice of alkyl-substituents on boron, the reactivity, regioselectivity, endo-stereo selectivity, and stability of vinylboranes can be optimized.

CYCLOHEXENOL ANNULATION VIA THE ALKOXY-ACCELERATED REARRANGEMENT OF VINYLCYCLOBUTANES

The lithium and potassium salts of 2-vinylcyclobutanols undergo vinylcyclobutane rearrangement at 25-70 gradC, providing an efficient method for the synthesis of 3-cyclohexenol derivatives. 2-Vinylcyclobutanones are prepared from α,β-unsaturated carbonyl