775356-24-6

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 2216-51-5 (-)-menthol 
• 107556-40-1 <4-<<(tert-butyldimethylsilyl)oxy>methyl>phenyl>magnesium bromide 
• 150766-59-9 1-bromo-4-((((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)methyl)benzene 
• 853654-21-4 1-(4-bromomethyl-phenyl)-1-methyl-siletane 
• 853654-20-3 [4-(1-methyl-siletan-1-yl)-phenyl]-methanol 
• 853654-19-0 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-1-methyl-siletane 

Downstream Products

• 548464-35-3 4-methoxybenzyl (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ether 
• 150766-59-9 1-bromo-4-((((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)methyl)benzene 
• 2216-51-5 (-)-menthol 

Relevant academic research and scientific papers

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

New strategies for protecting group chemistry: Synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers

Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The parasiletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions-involving alkaline hydrogen peroxide - that are unique among cleavage protocols for arylmethyl ethers. Furthermore, the PSB group affords the user new flexibility in the implementation of protecting group strategies that revolve around multiple arylmethyl ether protecting groups. In addition to hydrogen peroxide-based cleavage protocols, conversion of a PSB ether into a para-methoxybenzyl (PMB) ether and assembly of a PSB ether from a pre-existing para-bromobenzyl (PBB) ether are described. Finally, a new reagent for installing PSB ethers under neutral "mix and heat" conditions is reported.

The para-siletanylbenzyl (PSB) ether: A peroxide-cleavable protecting group for alcohols and phenols

A novel arylmethyl protecting group that is electronically similar to benzyl (Bn) but that can be cleaved under mild oxidizing conditions in the presence of para-methoxybenzyl (PMB) is described herein. para-Siletanylbenzyl (PSB) ethers are formed in one or two steps from the corresponding alcohols and cleaved in one or two steps with basic peroxide. Alcohols and phenols have been protected in good yields and deprotected cleanly under mild oxidative conditions.

Silica-supported sodium hydrogen sulfate catalyzed facile transformation of p-hydroxybenzyl alcohols to p-hydroxybenzyl ethers and thioethers

The heterogeneous catalyst, silica-supported sodium hydrogen sulfate (NaHSO4·SiO2) has been found to be highly efficient in carrying out the transformation of p-hydroxybenzyl alcohols at room temperature to p-hydroxybenzyl ethers and thioethers in very high yields.