A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent.

Chemical Science
Boya FengJingsong You

Abstract

Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread "inert" functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry.

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Citations

Jun 25, 2021·Bioorganic Chemistry·Janet Sabina XavierA Nityananda Shetty
Jul 8, 2021·Accounts of Chemical Research·Myuto Kashihara, Yoshiaki Nakao
Nov 12, 2020·Organic Letters·Masanori ShigenoYoshinori Kondo

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