Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles

Ming Chang P. Yeh; Chia Jung Liang; Tzu Lin Huang; Hsiao Ju Hsu; Yu Shuo Tsau

doi:10.1021/jo400634c

Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles

Ming Chang P. Yeh^*
, Chia Jung Liang
, Tzu Lin Huang
, Hsiao Ju Hsu
, Yu Shuo Tsau

^*Corresponding author for this work

Department of Chemistry

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

37 Citations (Scopus)

Abstract

The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl- protected N-containing cyclic enynols using inexpensive BF₃· OEt₂ is described. In this reaction, BF₃ reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp²)-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.

Original language	English
Pages (from-to)	5521-5529
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	78
Issue number	11
DOIs	https://doi.org/10.1021/jo400634c
Publication status	Published - 2013 Jun 7

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo400634c

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title = "Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles",

abstract = "The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl- protected N-containing cyclic enynols using inexpensive BF3· OEt2 is described. In this reaction, BF3 reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp2)-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.",

author = "Yeh, \{Ming Chang P.\} and Liang, \{Chia Jung\} and Huang, \{Tzu Lin\} and Hsu, \{Hsiao Ju\} and Tsau, \{Yu Shuo\}",

year = "2013",

month = jun,

day = "7",

doi = "10.1021/jo400634c",

language = "English",

volume = "78",

pages = "5521--5529",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols

T2 - Synthesis of fluorinated azabicycles

AU - Yeh, Ming Chang P.

AU - Liang, Chia Jung

AU - Huang, Tzu Lin

AU - Hsu, Hsiao Ju

AU - Tsau, Yu Shuo

PY - 2013/6/7

Y1 - 2013/6/7

N2 - The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl- protected N-containing cyclic enynols using inexpensive BF3· OEt2 is described. In this reaction, BF3 reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp2)-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.

AB - The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl- protected N-containing cyclic enynols using inexpensive BF3· OEt2 is described. In this reaction, BF3 reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp2)-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.

UR - https://www.scopus.com/pages/publications/84879296872

UR - https://www.scopus.com/pages/publications/84879296872#tab=citedBy

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AN - SCOPUS:84879296872

SN - 0022-3263

VL - 78

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EP - 5529

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles

Abstract

ASJC Scopus subject areas

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CCDC 926596: Experimental Crystal Structure Determination

CCDC 926589: Experimental Crystal Structure Determination

CCDC 926595: Experimental Crystal Structure Determination

Cite this

Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: Synthesis of fluorinated azabicycles

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 926596: Experimental Crystal Structure Determination

CCDC 926589: Experimental Crystal Structure Determination

CCDC 926595: Experimental Crystal Structure Determination

Cite this