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Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones.
Chemistry. 2015 Jan 19; 21(4):1468-73.C

Abstract

A copper-catalyzed difunctionalizing trifluoromethylation of activated alkynes with the cheap reagent sodium trifluoromethanesulfinate (NaSO2CF3 or Langlois' reagent) has been developed incorporating a tandem cyclization/dearomatization process. This strategy affords a straightforward route to synthesis of 3-(trifluoromethyl)-spiro[4.5]trienones, and presents an example of difunctionalization of alkynes for simultaneous formation of two carbon-carbon single bonds and one carbon-oxygen double bond.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hua HL
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-891-2582.
He YT
No affiliation info available
Qiu YF
No affiliation info available
Li YX
No affiliation info available
Song B
No affiliation info available
Gao P
No affiliation info available
Song XR
No affiliation info available
Guo DH
No affiliation info available
Liu XY
No affiliation info available
Liang YM
No affiliation info available

MeSH

AlkynesCatalysisCopperCyclizationHalogenationMethylationOxidation-ReductionSpiro Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25452200

Citation

Hua, Hui-Liang, et al. "Copper-catalyzed Difunctionalization of Activated Alkynes By Radical Oxidation-tandem Cyclization/dearomatization to Synthesize 3-trifluoromethyl Spiro[4.5]trienones." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 21, no. 4, 2015, pp. 1468-73.
Hua HL, He YT, Qiu YF, et al. Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones. Chemistry. 2015;21(4):1468-73.
Hua, H. L., He, Y. T., Qiu, Y. F., Li, Y. X., Song, B., Gao, P., Song, X. R., Guo, D. H., Liu, X. Y., & Liang, Y. M. (2015). Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones. Chemistry (Weinheim an Der Bergstrasse, Germany), 21(4), 1468-73. https://doi.org/10.1002/chem.201405672
Hua HL, et al. Copper-catalyzed Difunctionalization of Activated Alkynes By Radical Oxidation-tandem Cyclization/dearomatization to Synthesize 3-trifluoromethyl Spiro[4.5]trienones. Chemistry. 2015 Jan 19;21(4):1468-73. PubMed PMID: 25452200.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones. AU - Hua,Hui-Liang, AU - He,Yu-Tao, AU - Qiu,Yi-Feng, AU - Li,Ying-Xiu, AU - Song,Bo, AU - Gao,Pin, AU - Song,Xian-Rong, AU - Guo,Dong-Hui, AU - Liu,Xue-Yuan, AU - Liang,Yong-Min, Y1 - 2014/11/28/ PY - 2014/10/16/received PY - 2014/12/3/entrez PY - 2014/12/3/pubmed PY - 2015/9/25/medline KW - copper KW - cyclization KW - radical reactions KW - tandem reactions KW - trifluoromethylation SP - 1468 EP - 73 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 4 N2 - A copper-catalyzed difunctionalizing trifluoromethylation of activated alkynes with the cheap reagent sodium trifluoromethanesulfinate (NaSO2CF3 or Langlois' reagent) has been developed incorporating a tandem cyclization/dearomatization process. This strategy affords a straightforward route to synthesis of 3-(trifluoromethyl)-spiro[4.5]trienones, and presents an example of difunctionalization of alkynes for simultaneous formation of two carbon-carbon single bonds and one carbon-oxygen double bond. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25452200/Copper_catalyzed_difunctionalization_of_activated_alkynes_by_radical_oxidation_tandem_cyclization/dearomatization_to_synthesize_3_trifluoromethyl_spiro[4_5]trienones_ DB - PRIME DP - Unbound Medicine ER -