Publication:
Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF<inf>2</inf>SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

Issued Date

2018-01-19

Resource Type

Article

ISSN

15206904
00223263

DOI

10.1021/acs.joc.7b02783

Other identifier(s)

2-s2.0-85040832855

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.83, No.2 (2018), 765-782

Suggested Citation

Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF<inf>2</inf>SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines. Journal of Organic Chemistry. Vol.83, No.2 (2018), 765-782. doi:10.1021/acs.joc.7b02783 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45512

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Title

Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF<inf>2</inf>SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

Author(s)

Teerachai Punirun
 Darunee Soorukram
 Chutima Kuhakarn
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

Abstract

© 2017 American Chemical Society. An efficient C1-difluoromethylation of tetrahydroisoquinolenes was achieved using TMSCF2SPh as a difluoromethylating agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) as an oxidant. The process provides an access to a variety of C1-difluoro(phenylsulfanyl)methylated tetrahydroisoquinoline adducts in good yields. These adducts were employed as key precursors for preparing fluorinated pyrrolo[2,1-a]isoquinoline and benzo[a]quinolizidines.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/45512

Collections

Scopus 2018
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