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Synlett 2014; 25(15): 2149-2254
DOI: 10.1055/s-0034-1378516
DOI: 10.1055/s-0034-1378516
letter
Highly Efficient Direct Allylation of Oxindoles with Simple Allylic Alcohols Enabled by Palladium/Brønsted Acid Catalysis
Further Information
Publication History
Received: 19 May 2014
Accepted after revision: 16 June 2014
Publication Date:
25 August 2014 (online)
Abstract
A highly efficient and practical direct allylic alkylation of oxindoles with simple allylic alcohols cocatalyzed by Pd(OAc)2/Ph3P and PhCO2H under mild conditions has been developed, which streamlines the installation of an all-carbon quaternary allylic center at the oxindole 3-position. Enantioselective allylic alkylation has also been realized with the product in almost quantitative yield and 17% enantiomeric excess. Mechanistically, ESI analysis indicates that a palladium(0) species and π-allyl-Pd(PPh3)2 cation were involved.
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- 21 Typical Procedure To a flame-dried Schlenk tube charged with 4 Å MS (50 mg/0.1 mmol) and a magnetic stir bar was added 3-aryloxindoles 1 (0.1 mmol), allylic alcohol 2 (0.2 mmol), Pd(OAc)2 (3.0–10 mol%), Ph3P (3.0–10 mol%), and PhCOOH (3.0–10 mol%) in dry toluene (0.5 mL). The resulting suspension was stirred at the specified temperature under argon for 12 h. Upon completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and then quenched with sat. aq NH4Cl. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo, and purified by flash chromatography to afford pure products 3. tert-Butyl 3-Allyl-2-oxo-3-o-tolylindoline-1-carboxylate (3b) 1H NMR (400 MHz, CDCl3): δ = 1.61 (s, 9 H), 2.31 (s, 3 H), 3.02 (m, 2 H), 4.97 (m, 2 H), 5.42 (m, 1 H), 7.12 (m, 2 H), 7.22 (m, 3 H), 7.36 (m, 1 H), 7.91 (d, J = 8.4 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 21.31, 28.25, 28.84, 42.59, 55.92, 88.26, 115.04, 119.79, 125.71, 127.68, 128.71, 129.09, 130.58, 134.12, 137.66, 139.64, 149.46, 176.55. HRMS (EI): m/z calcd for C23H25NNaO3 [M + Na]+: 386.1729; found: 386.1727. tert-Butyl 3-Allyl-3-(2-methoxyphenyl)-2-oxoindoline-1-carboxylate (3c) 1H NMR (400 MHz, CDCl3): δ = 1.65 (s, 9 H), 3.01 (m, 2 H), 3.46 (s, 3 H), 4.97 (m, 2 H), 5.40 (m, 1 H), 6.78 (m, 2 H), 7.04 (m, 3 H), 7.23 (m, 1 H), 7.51 (m, 1 H), 7.81 (m, 1 H). 13C NMR (100 MHz, CDCl3): δ = 21.31, 28.25, 28.84, 42.59, 55.92, 88.26, 115.04, 119.79, 125.71, 127.68, 128.71, 129.09, 130.58, 134.12, 137.66, 139.64, 149.46, 176.55. HRMS (EI): m/z calcd for C23H25NNaO4 [M + Na]+: 402.1667; found: 402.1676. tert-Butyl 3-Allyl-2-oxo-3-m-tolylindoline-1-carboxylate (3d) 1H NMR (400 MHz, CDCl3): δ = 1.61 (s, 9 H), 2.31, (s, 3 H), 3.01 (m, 1 H), 3.11 (m, 1 H), 5.02 (m, 2 H), 5.40 (m, 1 H), 7.06 (m, 2 H), 7.21 (m, 4 H), 7.34 (m, 1 H), 7.93 (m, 1 H). 13C NMR (100 MHz, CDCl3): δ = 21.56, 21.61, 27.96, 28.09, 28.16, 42.55, 56.61, 84.27, 115.09, 119.70, 124.25, 124.32, 125.16, 127.86, 128.39, 130.53, 131.95, 138.24, 139.18, 139.83, 149.28, 176.33. HRMS (EI): m/z calcd for C20H21NNaO3 [M + Na]+: 346.1408; found: 346.1414.
For recent selected advances, see:
Another recent notable example for the direct allylation of α-branched aromatic aldehydes with allylic alcohols catalyzed by dual-catalytic strategy, see: