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

36 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

Access to Document

10.1021/jo400634c

Cite this

@article{f985cda6e2804843bcc93f73728aa5b7,

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",

number = "11",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=84879296872&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84879296872&partnerID=8YFLogxK

U2 - 10.1021/jo400634c

DO - 10.1021/jo400634c

M3 - Article

C2 - 23688341

AN - SCOPUS:84879296872

SN - 0022-3263

VL - 78

SP - 5521

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

Access to Document

Other files and links

Fingerprint

CCDC 926597: Experimental Crystal Structure Determination

CCDC 926594: Experimental Crystal Structure Determination

CCDC 926592: 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

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 926597: Experimental Crystal Structure Determination

CCDC 926594: Experimental Crystal Structure Determination

CCDC 926592: Experimental Crystal Structure Determination

Cite this