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

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

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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

Keywords

C-H functionalization
mechanochemistry
methylation
organometallics
late-stage functionalization

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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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publisher = "Wiley-VCH Verlag",

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Mechanochemical Solvent-Free Catalytic C—H Methylation. / Ni, Dr. Shengjun ; Hribersek, Matic ; Baddigam, Swarna K; Ingner, Fredric J. L; Orthaber, Dr. Andreas ; Gates, Paul J; Pilarski, Lukasz T.

In: Angewandte Chemie - International Edition, Vol. 60, No. 12, 15.03.2021, p. 6660 –6666 .

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

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)

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SP - 6660

EP - 6666

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 12

ER -

Mechanochemical Solvent-Free Catalytic C—H Methylation

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