Recent Progress in Methylation of (Hetero)Arenes by Cross-Coupling or C–H Activation

Lu Hu; Yahu A. Liu; Xuebin Liao

doi:10.1055/s-0037-1609093

Synlett, Table of Contents

Synlett 2018; 29(04): 375-382
DOI: 10.1055/s-0037-1609093

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Recent Progress in Methylation of (Hetero)Arenes by Cross-Coupling or C–H Activation

Lu Hu

^aDepartment of Pharmacology and Pharmaceutical Sciences, School of Medicine, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Tsinghua University, Beijing 100084, P. R. of China Email: liaoxuebin@mail.tsinghua.edu.cn

,

Yahu A. Liu *

^bDiscovery Chemistry, Genomics Institute of the Novartis Research Foundation, San Diego, CA 92121, USA Email: yliu2@gnf.org

,

Xuebin Liao *

^aDepartment of Pharmacology and Pharmaceutical Sciences, School of Medicine, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Tsinghua University, Beijing 100084, P. R. of China Email: liaoxuebin@mail.tsinghua.edu.cn

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Abstract

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Abstract

Owing to the ‘magic methyl effect’ on a compound’s physical and biological properties, methylation is a strategy frequently used by medicinal chemists in structure–activity relationship studies or in lead optimization. This article highlights the most recent reported methods for the direct methylation of (hetero)arenes, which mainly involve either C–H functionalization or cross-coupling of methylating reagents with (hetero)aryl halides. Methylation of C–H bonds of (hetero)-arenes, which is atom economical, has been explored by several research groups in recent years. Given the unmatchable availability of (hetero)aryl halides, we believe that Ni-catalyzed methylation using iodomethane or deuterated iodomethane as the methyl source is one of the most convenient methods.

Key words

methylation - methyl effect - iodomethane - C–H activation - aryl halides - cross-coupling - nickel catalysis

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References

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