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Synlett 2019; 30(08): 947-950
DOI: 10.1055/s-0037-1611477
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed [3+2] Cycloaddition of Vinylcyclopropane and Ketones

Wen-Ping Ding
a   The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, P. R. of China   Email: qinghaideng@shnu.edu.cn
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
,
Juan Du
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
,
Xiu-Yan Liu
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
,
Di Chen
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
,
Chang-Hua Ding  *
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: dingchanghua@shu.edu.cn
,
Qing-Hai Deng*
a   The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, P. R. of China   Email: qinghaideng@shnu.edu.cn
,
Xue-Long Hou*
b   State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, P. R. of China
d   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, SIOC, CAS, P. R. of China   Email: xlhou@sioc.ac.cn
› Author AffiliationsWe acknowledge financial support from the National Natural Science Foundation of China (NSFC) (21772215, 21532010, and 21472214), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20030100), the NSFC and the Research Grants Council of Hong Kong Joint Research Scheme (21361162001), the Chinese Academy of Sciences, the Technology Commission of Shanghai Municipality, and the Croucher Foundation of Hong Kong.
Further Information

Publication History

Received: 27 January 2019

Accepted after revision: 04 March 2019

Publication Date:
10 April 2019 (online)

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Abstract

A Pd-catalyzed [3+2] cycloaddition reaction of vinylcyclopropane and trifluoromethyl ketones as well as α-keto esters were developed, affording tetrahydrofurans in high yield.

Key words

palladium - [3+2] cycloaddition - vinylcyclopropane - trifluoromethyl ketone - α-keto ester - tetrahydrofuran

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1611477.
  • Supporting Information
 

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  • 10 General Experimental Procedures for Products 3 To a flame-dried sealing tube were added Pd(OAc)2 (2.25 mg, 0.01 mmol), (rac)-BINAP (12.45 mg, 0.02 mmol), and freshly distilled anhydrous tetrahydrofuran (1.0 mL). The resulting mixture was allowed to stir for 30 min. The ketone 2 (0.2 mmol) and vinylcyclopropane 1 (0.5 mmol) were added subsequently. The resulting reaction mixture was stirred at room temperature for 72 h. After the volatile was removed in vacuo, the ratio of two diastereoisomers was determined by crude 1H NMR analysis. The yield was determined by NMR spectroscopy using mesitylene as the internal standard. Then the resulting residue was purified by preparative TLC to afford pure sample for characterization. 2-Phenyl-2-(trifluoromethyl)-5-vinyldihydrofuran-3,3(2H)-dicarbonitrile (3a) White solid, mp 48.5–48.7 °C, yield 89%, dr 1.3:1. 1H NMR (400 MHz in CDCl3; taken as a mixture of diastereomers): δ (minor diastereomer) = 7.70–7.75 (m, 2 H), 7.48–7.52 (m, 3 H), 5.96 (ddd, J = 17.2, 10.0, 6.8 Hz, 1 H), 5,51 (d, J = 18.4 Hz, 1 H), 5.38 (d, J = 10.4 Hz, 1 H), 5.07–4.99 (m, 1 H), 3.09–3.01 (m, 1 H), 2.88 (dd, J = 13.6, 8.4 Hz, 1 H); δ (major diastereomer) = 6.03 (ddd, J = 17.2, 10.0, 6.8 Hz, 1 H), 5.55 (d, J = 18.4 Hz, 1 H), 5.45 (d, J = 10.4 Hz, 1 H), 5.21–5.12 (m, 1 H), 3.31 (dd, J = 13.6, 8.4 Hz, 1 H), 2.87–2.79 (m, 1 H). 13C NMR (101 MHz in CDCl3; taken as a mixture of diastereomers): δ = 134.8, 133.0, 132.4, 132.0, 130.7 (2 C), 129.0, 128.9, 126.5, 126.4, 124.8 (q, J = 291 Hz), 124.1 (q, J = 291 Hz), 120.9, 119.9, 112.7, 112.2, 111.7, 111.1, 90.3 (q, J = 29 Hz, 2 C), 81.7, 44.3 (2 C), 43.8, 42.2.19F NMR (376 MHz in CDCl3; taken as a mixture of diastereomers): δ = –72.32, –74.07. IR (film): 1450, 1348, 1267, 1192, 1156, 1117, 1104, 1066, 1032, 1015, 999, 983, 942, 763, 725, 697 cm–1. GC–MS (EI): m/z (rel.): 292 [M+], 223, 175 (100), 118, 105, 91, 77. HRMS (EI): m/z calcd for C15H11F3N2O [M+]: 292.0823; found: 292.0832.