38064-90-3Relevant articles and documents
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
supporting information, 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.
A solvent-controlled highly efficient Pd-C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes via a novel 'acetal pathway'
Xing, Lixin,Wang, Xinyan,Cheng, Chuanjie,Zhu, Rui,Liu, Bo,Hu, Yuefei
, p. 9382 - 9386 (2008/02/10)
Pd-C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes has been described to proceed via a 'benzenemethanol pathway'. In this article, a novel 'acetal pathway' was first revealed by a systematic study when lower alcohols were used as solvents and a solvent-controlled highly efficient procedure was established.
The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid
Patterson, John W.
, p. 4542 - 4548 (2007/10/02)
Mycophenolic acid (1) has been synthesized from 2,4-dihydroxybenzoic acid by regioselective introduction of the three required carbon substituents.A key transformation in this sequence is the introduction of the methyl substituent at position 5 by a rapid, uncatalyzed replacement of the bromide in 8 at low temperature by methyllithium.The scope and mechanism of this methylation reaction are examined.