103826-49-9

Upstream product

• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 78-79-5 isoprene 
• 72863-20-8 α,α-Dimethylallyl phenyl sulfone 
• 769-92-6 4-tert-Butylaniline 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 109347-45-7 2-(4-(tert-butyl)phenyl)acetaldehyde 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 129813-21-4 2-(1,1-dimethyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 870-63-3 prenyl bromide 
• 123324-71-0 p-tert-butylphenylboronic acid 

Relevant academic research and scientific papers

A General Photocatalytic Route to Prenylation

Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop-in solution for prenylation, expanding the scope of substrates that can be readily prenylated.

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%).

Pd(0)-CATALYZED ELECTRO-REDUCTIVE HYDROCOUPLING OF ARYL HALIDES WITH OLEFINS AND ACETYLENES

Electro-reductive hydrocoupling of aryl halides with olefins and acetylenes has been performed in an Et4NOTs-DMF-(Pb cathode) system in the presence of catalytic amounts of PdCl2(Ph3P)2.