Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

Teerachai Punirun; Darunee Soorukram; Chutima Kuhakarn; Vichai Reutrakul; Manat Pohmakotr

doi:10.1021/acs.joc.7b02783

Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF₂SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

Teerachai Punirun
, Darunee Soorukram
, Chutima Kuhakarn
, Vichai Reutrakul
, Manat Pohmakotr

Mahidol University

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

34 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	765-782
Number of pages	18
Journal	Journal of Organic Chemistry
Volume	83
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.7b02783
Publication status	Published - 19 Jan 2018
Externally published	Yes

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title = "Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines",

abstract = "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.",

author = "Teerachai Punirun and Darunee Soorukram and Chutima Kuhakarn and Vichai Reutrakul and Manat Pohmakotr",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.joc.7b02783",

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T1 - Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF2SPh

T2 - Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

AU - Punirun, Teerachai

AU - Soorukram, Darunee

AU - Kuhakarn, Chutima

AU - Reutrakul, Vichai

AU - Pohmakotr, Manat

PY - 2018/1/19

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AB - 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.

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DO - 10.1021/acs.joc.7b02783

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AN - SCOPUS:85040832855

SN - 0022-3263

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Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF₂SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

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