Compound 2ca
3-(4-(tert-butyl)-2,6-dibutylbenzyl)benzofuran
From: Remote C−H alkylation and C−C bond cleavage enabled by an in situ generated palladacycle
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Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
The title compound was prepared according to the same general procedure outlined in the synthesis of 2aa. 2ca (63.9 mg, 56%) was obtained as an oil under room temperature and became a white solid after storing in a -20 oC freezer overnight (crystal suitable for X-ray analysis was obtained from a solution of hexane stored in a -20 oC freezer, m.p. < 40 oC): 1H NMR (400 MHz, CDCl3) δ = 7.63-7.57 (m, 1 H, Ar-H), 7.47-7.42 (m, 1 H, Ar-H), 7.33-7.22 (m, 2 H, Ar-H), 7.08 (s, 2 H, Ar-H), 6.83 (t, J = 1.4 Hz, 1 H, C=CH), 3.95 (d, J = 1.6 Hz, 2 H, CH2C=), 2.61-2.51 (m, 4 H, two CH2 from n-Bu), 1.58-1.46 (m, 4 H, two CH2 from n-Bu), 1.38-1.24 (m, 13 H, nine protons from tBu and two CH2 from n-Bu), 0.85 (t, J = 7.4 Hz, 6 H, two CH3 from n-Bu); 13C NMR (100 MHz, CDCl3) δ = 155.5, 148.9, 142.4, 141.0, 131.3, 128.2, 124.2, 124.1, 122.2, 120.6, 119.4, 111.4, 34.3, 33.9, 33.5, 31.4, 22.84, 22.81, 14.0; IR (CHCl3, cm-1) 2957, 2930, 2870, 1574, 1479, 1464, 1452, 1361, 1277, 1182, 1092; HRMS (DART) calculated for C27H37O [M+H+]: 377.28444, found: 377.28502.
