Mechanochemical Solvent-Free Catalytic C—H Methylation

Dr. Shengjun  Ni; Matic  Hribersek; Swarna K Baddigam; Fredric J. L Ingner; Dr. Andreas  Orthaber; Paul J Gates; Lukasz T Pilarski

doi:10.1002/anie.202010202

Mechanochemical Solvent-Free Catalytic C—H Methylation

Dr. Shengjun Ni
, Matic Hribersek
, Swarna K Baddigam
, Fredric J. L Ingner
, Dr. Andreas Orthaber
, Paul J Gates
, Lukasz T Pilarski^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

117 Citations (Scopus)

228 Downloads (Pure)

Abstract

The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C–H methylation of (hetero)arenes is reported. The reaction shows excellent functional group compatibility and is demonstrated to work for the late-stage C–H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C–H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.

Original language	English
Pages (from-to)	6660 –6666
Number of pages	7
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	12
DOIs	https://doi.org/10.1002/anie.202010202
Publication status	Published - 15 Mar 2021

Research Groups and Themes

Organic & Biological

Keywords

C-H functionalization
mechanochemistry
methylation
organometallics
late-stage functionalization

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10.1002/anie.202010202

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title = "Mechanochemical Solvent-Free Catalytic C—H Methylation",

abstract = "The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C–H methylation of (hetero)arenes is reported. The reaction shows excellent functional group compatibility and is demonstrated to work for the late-stage C–H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C–H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.",

keywords = "C-H functionalization, mechanochemistry, methylation, organometallics, late-stage functionalization",

author = "Ni, \{Dr. Shengjun\} and Matic Hribersek and Baddigam, \{Swarna K\} and Ingner, \{Fredric J. L\} and Orthaber, \{Dr. Andreas\} and Gates, \{Paul J\} and Pilarski, \{Lukasz T\}",

year = "2021",

month = mar,

day = "15",

doi = "10.1002/anie.202010202",

language = "English",

volume = "60",

pages = "6660 –6666 ",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Mechanochemical Solvent-Free Catalytic C—H Methylation

AU - Ni, Dr. Shengjun

AU - Hribersek, Matic

AU - Baddigam, Swarna K

AU - Ingner, Fredric J. L

AU - Orthaber, Dr. Andreas

AU - Gates, Paul J

AU - Pilarski, Lukasz T

PY - 2021/3/15

Y1 - 2021/3/15

N2 - The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C–H methylation of (hetero)arenes is reported. The reaction shows excellent functional group compatibility and is demonstrated to work for the late-stage C–H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C–H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.

AB - The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C–H methylation of (hetero)arenes is reported. The reaction shows excellent functional group compatibility and is demonstrated to work for the late-stage C–H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C–H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.

KW - C-H functionalization

KW - mechanochemistry

KW - methylation

KW - organometallics

KW - late-stage functionalization

U2 - 10.1002/anie.202010202

DO - 10.1002/anie.202010202

M3 - Article (Academic Journal)

C2 - 33031646

SN - 1433-7851

VL - 60

SP - 6660

EP - 6666

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Mechanochemical Solvent-Free Catalytic C—H Methylation

Abstract

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Keywords

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