Silane-mediated, facile C-H and N-H methylation using formaldehyde

Jabir Khan; Neha Taneja; Naveen Yadav; Chinmoy Kumar Hazra

doi:10.1039/d4cc03976a

Silane-mediated, facile C-H and N-H methylation using formaldehyde

Jabir Khan
, Neha Taneja
, Naveen Yadav
, Chinmoy Kumar Hazra^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

The use of (para)-formaldehyde for the methylation/alkylation of C(sp²)-H and N-H bonds, utilizing a combination of silane and hexafluoroisopropanol (HFIP) as activators, is reported. Overcoming the complexity of C(sp²)-H methylation on aryl and indole substrates, the process utilizes a Friedel-Crafts alkylation, followed by silane as a hydride donor, under a mild acidic medium. The method has been employed for the synthesis of the antifungal drug butenafine and a derivative of the non-steroidal anti-inflammatory drug (NSAID) flurbiprofen.

Original language	English
Pages (from-to)	11367-11370
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	80
DOIs	https://doi.org/10.1039/d4cc03976a
State	Published - 9 Sep 2024
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2024 The Royal Society of Chemistry.

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Silane-mediated, facile C-H and N-H methylation using formaldehyde",

abstract = "The use of (para)-formaldehyde for the methylation/alkylation of C(sp2)-H and N-H bonds, utilizing a combination of silane and hexafluoroisopropanol (HFIP) as activators, is reported. Overcoming the complexity of C(sp2)-H methylation on aryl and indole substrates, the process utilizes a Friedel-Crafts alkylation, followed by silane as a hydride donor, under a mild acidic medium. The method has been employed for the synthesis of the antifungal drug butenafine and a derivative of the non-steroidal anti-inflammatory drug (NSAID) flurbiprofen.",

author = "Jabir Khan and Neha Taneja and Naveen Yadav and Hazra, \{Chinmoy Kumar\}",

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year = "2024",

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doi = "10.1039/d4cc03976a",

language = "English",

volume = "60",

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AU - Khan, Jabir

AU - Taneja, Neha

AU - Yadav, Naveen

AU - Hazra, Chinmoy Kumar

PY - 2024/9/9

Y1 - 2024/9/9

N2 - The use of (para)-formaldehyde for the methylation/alkylation of C(sp2)-H and N-H bonds, utilizing a combination of silane and hexafluoroisopropanol (HFIP) as activators, is reported. Overcoming the complexity of C(sp2)-H methylation on aryl and indole substrates, the process utilizes a Friedel-Crafts alkylation, followed by silane as a hydride donor, under a mild acidic medium. The method has been employed for the synthesis of the antifungal drug butenafine and a derivative of the non-steroidal anti-inflammatory drug (NSAID) flurbiprofen.

AB - The use of (para)-formaldehyde for the methylation/alkylation of C(sp2)-H and N-H bonds, utilizing a combination of silane and hexafluoroisopropanol (HFIP) as activators, is reported. Overcoming the complexity of C(sp2)-H methylation on aryl and indole substrates, the process utilizes a Friedel-Crafts alkylation, followed by silane as a hydride donor, under a mild acidic medium. The method has been employed for the synthesis of the antifungal drug butenafine and a derivative of the non-steroidal anti-inflammatory drug (NSAID) flurbiprofen.

UR - https://www.scopus.com/pages/publications/85205603617

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EP - 11370

JO - Chemical Communications

JF - Chemical Communications

IS - 80

ER -

Silane-mediated, facile C-H and N-H methylation using formaldehyde

Abstract

Bibliographical note

ASJC Scopus subject areas

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