A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid–base activation

Efficient Approach for the Tritylation of Alcohols Using Recyclable Lewis Acid-Based Ionic Liquid (EMIM·AlCl4)

“…Tritylation of alcohols as trityl ether were generally carried out by reaction of alcohols with triphenyl methyl halides in the presence of base, − such as pyridine, 4-dimethylaminopyridine, 2,4,6-collidine, triethylamine, and 1,8-diazabicyclo[5.4.0]­undec-7-ene. There are limited reports in the literature where triphenyl methanol (Tr-OH) was used for protection of alcohols as trityl ethers − in the presence of an acidic catalyst.…”

Development of a Storable Triazinone-Based Reagent forO-p-Methoxybenzylation under Mild Heating Conditions

“…In fact, addition of a stabilizer (potassium or calcium carbonate) is required to prevent autocatalytic production of HCl gas, which may cause overpressurization and rupture of containers. To overcome the problems of PMB chloride, a number of O - p -methoxybenzylating reagents have been developed in the past few decades. − For example, PMB 2,2,2-trichloroacetimidate (PMB-TCAI, Figure ) is widely used to introduce the PMB group under nonbasic conditions, although the stability of this reagent is not satisfactory for long-term storage. In 2013, we reported 2,4,6-tris­( p -methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM, Figure ) as a stable and easy-to-handle reagent for PMB ether synthesis .…”

“…In 2013, we reported 2,4,6-tris­( p -methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM, Figure ) as a stable and easy-to-handle reagent for PMB ether synthesis . However, these reagents require an activator such as a Brønsted/Lewis acid − or an electrophile − for the reaction. Because of this, the limitation of functional group compatibility is still inevitable.…”