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Si-DPP (R39030B) is available at SiliCycle (www.silicycle.com).
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Si-DPP (R39030B) is available at SiliCycle (www.silicycle.com).
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46
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62249216133
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Experimental Procedure In a typical experiment, a THF (0.5 mL) solution of Rh(acac)(coe)2 (8 mg, 0.019 mmol) was added to a THF (2 mL) slurry of Si-DPP (60 mg, 0.056 mmol, and the mixture was stirred for 5 h. To this mixture was added a THF (0.5 mL) solution of 2-vinylnaphthalene (135 mg, 0.87 mmol) followed by a THF (0.5 mL) solution of HBcat (126 mg, 1.05 mmol, The reaction was allowed to proceed for 18 h at which point the mixture was filtered through a small plug of Celite before solvent was removed under vacuum. The residual oil was dissolved in C6D6 (1 mL) and analyzed by multinuclear NMR spectroscopy.5a,10 Confirmation of product formation was carried out using GC-MS on products derived from a basic, oxidative workup. Selected NMR Spectroscopic Data 4-MeOC 6H4CH(Bcat)Me (i; R, OMe; Bcat, 1H NMR 270 MHz, C6D6, δ, 2.74 [q, J, 7.7 Hz, CH
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2].
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0001411843
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Selected NMR Spectroscopic Data 4-MeOC6H 4CH(Bpin)Me (i; R, OMe; Bpin, 1H NMR (270 MHz, C6D6, δ, 2.56 [q, J, 7.7 Hz, CH(Bpin)CH3, 1.50 [d, J, 7.7 Hz, CH(Bpin)CH3, 4-MeOC6H4CH2CH 2(Bpin, ii; R, OMe; Bpin, 1H NMR (270 MHz, C6D6, δ, 2.87 [t, J, 7.9 Hz, CH2CH2 (Bpin, 1.12 [t, J, 7.9 Hz, CH 2CH2(Bpin, 4-MeOC6H 4CH=CH(Bpin, iii; R, OMe; Bpin, 1H NMR (270 MHz, C6D6, δ, 7.80 [d, J, 18.3 Hz, CH=CH(Bpin, 6.40 [d, J, 18.3 Hz, CH=CH(Bpin, 4-FC 6H4CH(Bpin)Me (i; R, F; Bpin, 1H NMR 270 MHz, C6D6, δ, 2.45 [q, J, 7.7
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Selected NMR Spectroscopic Data 2,4,6-Me3C 6H2CH(Bcat)Me (v, 1H NMR (270 MHz, C6D6, δ, 2.90 [q, J, 7.7 Hz, CH(Bcat)CH3, 1.42 [d, J, 7.7 Hz, CH(Bcat)CH3, 2,4,6-Me3C6H2CH 2CH2(Bcat, vi, 1H NMR (270 MHz, C 6D6, δ, 2.81 [t, J, 7.9 Hz, CH 2CH2 (Bcat, 1.31 [t, J, 7.9 Hz, CH 2CH2 (Bcat, 2,4,6-Me3C 6H2CH=CH(Bcat, vii, 1H NMR (270 MHz, C6D6, δ, 7.90 [d, J, 18.3 Hz, CH=CH(Bcat, 6.10 [d, J, 18.3 Hz, CH=CH(Bcat, 2,4,6-Me3C6H2CH2CH(Bcat) 2 (viii, 1H NMR 270 MHz, C6D 6
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2].
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