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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

37 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	5521-5529
頁數	9
期刊	Journal of Organic Chemistry
卷	78
發行號	11
DOIs	https://doi.org/10.1021/jo400634c
出版狀態	已發佈 - 2013 6月 7

ASJC Scopus subject areas

有機化學

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10.1021/jo400634c

其它文件與鏈接

CCDC 926596: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Liang, C.-J. (Creator), Huang, T.-L. (Creator), Hsu, H.-J. (Creator) & Tsau, Y.-S. (Creator), Unknown Publisher, 2013
DOI: 10.5517/cc10366j, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10366j&sid=DataCite
資料集: Dataset
CCDC 926592: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Liang, C.-J. (Creator), Huang, T.-L. (Creator), Hsu, H.-J. (Creator) & Tsau, Y.-S. (Creator), Unknown Publisher, 2013
DOI: 10.5517/cc10362d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10362d&sid=DataCite
資料集: Dataset
CCDC 926593: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Liang, C.-J. (Creator), Huang, T.-L. (Creator), Hsu, H.-J. (Creator) & Tsau, Y.-S. (Creator), Unknown Publisher, 2013
DOI: 10.5517/cc10363f, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10363f&sid=DataCite
資料集: Dataset

引用此

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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",

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T2 - Synthesis of fluorinated azabicycles

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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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 926596: Experimental Crystal Structure Determination

CCDC 926592: Experimental Crystal Structure Determination

CCDC 926593: Experimental Crystal Structure Determination

引用此