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Synlett 2018; 29(06): 840-844
DOI: 10.1055/s-0036-1591748
letter
© Georg Thieme Verlag Stuttgart · New York

NHPI- and TBAI-Co-Catalyzed Synthesis of Allylic Esters from Toluene Derivatives and Alkenes

Chengliang Li
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
,
Hongmei Deng*
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China   Email: hmdeng@staff.shu.edu.cn
,
Tao Jin
c   Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Chunju Li
c   Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Xueshun Jia*
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
c   Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Jian Li*
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
c   Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
› Author AffiliationsWe thank the National Natural Science Foundation of China (Nos: 21472121, 21272148) for financial support.
Further Information

Publication History

Received: 29 October 2017

Accepted after revision: 06 December 2017

Publication Date:
15 January 2018 (online)

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Abstract

An N-hydroxyphthalimide (NHPI) and tetrabutylammonium iodide (TBAI) co-catalyzed oxidative coupling reaction of toluene derivatives and alkenes has been disclosed. This method can serve as a new strategy to access allylic ester using toluene derivatives as oxyacylating reagent. This metal-free protocol also features the readily available starting materials, broad substrate scope, and mild reaction conditions.

Key words

oxyacylation - toluene derivatives - oxidative coupling - ­allylic ester - metal-free

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591748.
  • Supporting Information
 

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  • 22 Experimental Procedure and Characterization Data A 50 mL three-necked round-bottom flask equipped with a magnetic stir bar was charged with toluene derivatives 2 (3.0 mmol), olefin 1 (1.0 mmol), NHPI (16.3 mg, 10 mol%), and Bu4NI (36.9 mg, 10 mol%) in MeCN (8 mL) at room temperature. O2 was bubbled into the mixture at 75 °C for 6–12 h. After the reaction was completed, it was monitored by TLC. The resulting solution was poured into NaCl (15 mL), extracted with DCM (twice). The combined organic layers were dried over anhydrous Na2SO4 and solvents were removed in vacuo. The residue was purified by PLC Silica gel plate (eluent: petroleum ether/ethyl acetate = 30:1) to give the desired product. Compound 3a: 123 mg, 61% yield; colorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.07–8.05 (m, 2 H), 7.56–7.52 (m, 1 H), 7.44–7.41 (m, 2 H), 6.02–5.98 (m, 1 H), 5.86–5.82 (m, 1 H), 5.52–5.51 (m, 1 H), 2.17–2.10 (m, 1 H), 2.08–2.02 (m, 2 H), 1.94–1.92 (m, 2 H),1.74–1.61 (m, 1 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 166.2, 132.8, 132.7, 130.8, 129.6, 128.3, 125.7, 68.6, 28.4, 24.9, 18.9 ppm.