773873-94-2Relevant academic research and scientific papers
Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source
Wu, Zhuo,Wei, Feng,Wan, Bin,Zhang, Yanghui
, p. 4524 - 4530 (2021/05/04)
A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.
Synthesis of N-(3′,5′-dimethyl-4′-hydroxybenzyl)-N-tosy 1-3,4-dimethoxybenzyl amine
China Raju,Neelakantan, Parvathi,Bhalerao
, p. 201 - 203 (2008/02/09)
Reaction of 4-benzyloxy-3,5-dimethyl benzyl bromide 4 and N-tosyl-3,4-dimethoxy benzyl amine 5 gives the N-(4′-benzyloxy3′, 5′-dimethylbenzyl)-N-tosyl-3,4-dimethoxybenzyl amine 6. The obtained product on debenzylation affords N-(3′,5′-dimethyl-4′- hydroxy
