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Synlett 2018; 29(06): 840-844
DOI: 10.1055/s-0036-1591748
DOI: 10.1055/s-0036-1591748
letter
NHPI- and TBAI-Co-Catalyzed Synthesis of Allylic Esters from Toluene Derivatives and Alkenes
We 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)
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.
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.
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