93930-23-5

Upstream product

• 870-63-3 prenyl bromide 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 141550-13-2 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 20329-96-8 methyl 3,4,5-trimethoxycinnamate 
• 53560-25-1 methyl 3-(3,4,5-trimethoxyphenyl)propionate 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 272124-87-5 [(E)-2-(3,4,5-Trimethoxy-phenyl)-vinyl]-phosphonic acid diethyl ester 
• 93930-22-4 2-methyl-4-(3,4,5-trimethoxyphenyl)butan-2-ol 

Relevant academic research and scientific papers

Ligand-controlled palladium-catalyzed regiodivergent suzuki-miyaura cross-coupling of allylboronates and aryl halides

An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the

Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates

This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners. The Royal Society of Chemistry 2013.

Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and 5 M KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed (E/Z & 80/20).

Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions

This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%).

Heck reactions using aryldiazonium salts towards phosphonic derivatives

A facile synthesis of aryl vinylphosphonates has been based on Heck reaction of aryldiazonium salts bearing electrowithdrawing or donating groups with vinylphosphonates. A one-pot procedure consisting of Heck reaction and hydrogenation permits the clean f

1-(3,4-DIHYDROXY-5-METHOXYPHENYL)-3-METHYLBUT-2-ENE FROM THE LIVERWORT PLAGIOCHILA RUTILANS

Extraction of the liverwort Plagiochila rutilans afforded 1-(3,4-dihydroxy-5-methoxyphenyl)-3-methylbut-2-ene, the structure of which was confirmed by synthesis. - Key Word Index: Plagiochila rutilans; Hepaticae; 1-(3,4-dihydroxy-5-methoxyphenyl)-3-methyl